GB636988A - Improvements in and relating to the production of colour photographic images - Google Patents
Improvements in and relating to the production of colour photographic imagesInfo
- Publication number
- GB636988A GB636988A GB34274/47A GB3427447A GB636988A GB 636988 A GB636988 A GB 636988A GB 34274/47 A GB34274/47 A GB 34274/47A GB 3427447 A GB3427447 A GB 3427447A GB 636988 A GB636988 A GB 636988A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolone
- amino
- phenyl
- prepared
- heating
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- 238000010438 heat treatment Methods 0.000 abstract 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- QKLMWNVNJBXKRG-UHFFFAOYSA-N 5-phenyl-3h-1,3-benzoxazole-2-thione Chemical compound C=1C=C2OC(=S)NC2=CC=1C1=CC=CC=C1 QKLMWNVNJBXKRG-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- GFPJLZASIVURDY-UHFFFAOYSA-N (3-chlorophenyl)hydrazine Chemical compound NNC1=CC=CC(Cl)=C1 GFPJLZASIVURDY-UHFFFAOYSA-N 0.000 abstract 1
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical compound C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 abstract 1
- BNXILSHVRIETJN-UHFFFAOYSA-N 2-chloro-5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC(Cl)=NC2=CC=1C1=CC=CC=C1 BNXILSHVRIETJN-UHFFFAOYSA-N 0.000 abstract 1
- LYLPTGBYMDITGN-UHFFFAOYSA-N 4-(3-amino-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(N)=NN1C1=CC=C(S(O)(=O)=O)C=C1 LYLPTGBYMDITGN-UHFFFAOYSA-N 0.000 abstract 1
- VROZMOZSNFUILE-UHFFFAOYSA-N 5-amino-2-(3-chlorophenyl)-4h-pyrazol-3-one Chemical compound O=C1CC(N)=NN1C1=CC=CC(Cl)=C1 VROZMOZSNFUILE-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 abstract 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229940117953 phenylisothiocyanate Drugs 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 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
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F27—FURNACES; KILNS; OVENS; RETORTS
- F27D—DETAILS OR ACCESSORIES OF FURNACES, KILNS, OVENS OR RETORTS, IN SO FAR AS THEY ARE OF KINDS OCCURRING IN MORE THAN ONE KIND OF FURNACE
- F27D3/00—Charging; Discharging; Manipulation of charge
- F27D3/12—Travelling or movable supports or containers for the charge
- F27D3/123—Furnace cars
Landscapes
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
1 - Phenyl - 3 - [4 - chloroquinolyl - (2) - amino]-5-pyrazolone is prepared by refluxing together 1-phenyl-3-amino-5-pyrazolone and 2 : 4-dichloroquinoline in glacial acetic acid. 1 - Phenyl - 3 - [benzoxazolyl - (2) - amino] - 5 - pyrazolone is prepared by heating together 1-phenyl-3-amino-5-pyrazolone and 2-chlorobenzoxazole. 1-Phenyl-3-[5-phenylbenzoxazolyl-(2)-amino]-5-pyrazolone and 1-phenyl-3-[benzselenazolyl - (2) - amino] - 5 - pyrazolone are similarly prepared. 1 - Phenyl - 3 - [benzthiazolyl - (2) - amino] - 5 - pyrazolone is prepared by refluxing together 1-phenyl-3-amino-5-pyrazolone, phenyl isothiocyanate, and pyridine, acidifying, adding a chloroform solution of bromine to a chloroform solution of the precipitate, heating, dissolving in aqueous NaOH and heating, and precipitating with acetic acid. 1-Benzthiazolyl-(2)-3-[benzthiazolyl-(2)-amino]-5-pyrazolone and ethyl-3-[benzthiazolyl - (2) - amino] - 5 - pyrazolone - 1 - acetate are similarly prepared. Bis - [1 - m - chlorophenyl - 5 - pyrazolonyl - (3)]-amine is prepared by reacting ethyl malonate mono-imido ether with m-chlorophenylhydrazine, and removing the 1-m-chlorophenyl-3-amino-5-pyrazolone also formed. 2-Mercapto-5-phenylbenzoxazole is prepared by boiling 4-hydroxy-3-aminodiphenyl with KOH and CS2 in ethyl alcohol. 2-Chloro-5-phenylbenzoxazole is prepared by heating 2-mercapto-5-phenylbenzoxazole with PCl5 and POCl3. The ammonium salt of 1-p-sulphophenyl-3-[21-chloroquinazolyl-(41) -amino]-5-pyrazolone is prepared by heating together the ammonium salt of 1-p-sulphophenyl-3-amino-5-pyrazolone and 2 : 4-dichloroquinazoline in aqueous ethyl alcohol.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34274/47A GB636988A (en) | 1947-12-24 | 1947-12-24 | Improvements in and relating to the production of colour photographic images |
| US66837A US2619419A (en) | 1947-12-24 | 1948-12-22 | Production of color photographic images |
| FR978214D FR978214A (en) | 1947-12-24 | 1948-12-24 | Process for the production of color photographic images |
| DEG458A DE812874C (en) | 1947-12-24 | 1949-11-23 | Process for the production of color photographic images |
| DEG4905A DE848011C (en) | 1947-12-24 | 1950-12-28 | Process for the production of color photographic images |
| FR62605D FR62605E (en) | 1947-12-24 | 1950-12-29 | Process for the production of color photographic images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34274/47A GB636988A (en) | 1947-12-24 | 1947-12-24 | Improvements in and relating to the production of colour photographic images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB636988A true GB636988A (en) | 1950-05-10 |
Family
ID=42342840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34274/47A Expired GB636988A (en) | 1947-12-24 | 1947-12-24 | Improvements in and relating to the production of colour photographic images |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2619419A (en) |
| DE (2) | DE812874C (en) |
| FR (2) | FR978214A (en) |
| GB (1) | GB636988A (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE526445A (en) * | 1953-02-13 | |||
| BE643149A (en) * | 1964-01-30 | 1964-07-30 | ||
| US4061653A (en) * | 1972-06-23 | 1977-12-06 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
| US4032646A (en) * | 1973-04-17 | 1977-06-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| AR207444A1 (en) * | 1973-04-17 | 1976-10-08 | Bayer Ag | PROCEDURE FOR THE PRODUCTION OF NEW PYRAZOLONES- (5) 1-SUBSTITUTED |
| US4081596A (en) * | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| DE2319278C2 (en) * | 1973-04-17 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Pharmaceutical agent |
| US4000294A (en) * | 1973-04-17 | 1976-12-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4045571A (en) * | 1973-04-17 | 1977-08-30 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4056533A (en) * | 1973-04-17 | 1977-11-01 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US3992404A (en) * | 1973-04-17 | 1976-11-16 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| AR207445A1 (en) * | 1973-04-17 | 1976-10-08 | Bayer Ag | PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF PIRAZOLONES- (5) -1-SUBSTITUTED |
| US4005215A (en) * | 1973-04-17 | 1977-01-25 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| US4069334A (en) * | 1973-12-20 | 1978-01-17 | Bayer Aktiengesellschaft | Pyrazole derivatives |
| DE2363511A1 (en) * | 1973-12-20 | 1975-07-10 | Bayer Ag | PYRAZOLE DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT |
| DE2427272C3 (en) * | 1974-06-06 | 1981-10-01 | Bayer Ag, 5090 Leverkusen | 1- (2- (β-Naphthyloxy) ethyl) -3-methyl-pyrazolone- (5), method and use as an antithrombotic |
| US4268592A (en) * | 1978-09-07 | 1981-05-19 | Ciba-Geigy Ag | Material for color photography |
| EP1781637A1 (en) * | 2004-06-29 | 2007-05-09 | Rigel Pharmaceuticals, Inc. | 2-substituted quinoline compounds and their uses as inhibitors of the ige receptor signaling cascade |
| WO2010039186A2 (en) * | 2008-09-23 | 2010-04-08 | Renovis, Inc. | Compounds useful as faah modulators and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2376380A (en) * | 1945-05-22 | Preparation of amino pyrazolones | ||
| US2179239A (en) * | 1935-04-10 | 1939-11-07 | Agfa Ansco Corp | Color photography |
| 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 |
| US2294909A (en) * | 1939-02-13 | 1942-09-08 | Du Pont | Chemical process and composition |
| US2311082A (en) * | 1941-11-14 | 1943-02-16 | Eastman Kodak Co | Pyrazolone coupler for color photography |
| GB553506A (en) * | 1941-11-20 | 1943-05-25 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| US2343703A (en) * | 1942-09-04 | 1944-03-07 | Eastman Kodak Co | Pyrazolone coupler for color photography |
-
1947
- 1947-12-24 GB GB34274/47A patent/GB636988A/en not_active Expired
-
1948
- 1948-12-22 US US66837A patent/US2619419A/en not_active Expired - Lifetime
- 1948-12-24 FR FR978214D patent/FR978214A/en not_active Expired
-
1949
- 1949-11-23 DE DEG458A patent/DE812874C/en not_active Expired
-
1950
- 1950-12-28 DE DEG4905A patent/DE848011C/en not_active Expired
- 1950-12-29 FR FR62605D patent/FR62605E/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2619419A (en) | 1952-11-25 |
| FR62605E (en) | 1955-06-15 |
| DE848011C (en) | 1952-09-18 |
| FR978214A (en) | 1951-04-11 |
| DE812874C (en) | 1951-09-06 |
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