GB837360A - 6-amino-8-hydroxyquinolines as coupling components for azine dye images - Google Patents
6-amino-8-hydroxyquinolines as coupling components for azine dye imagesInfo
- Publication number
- GB837360A GB837360A GB5146/58A GB514658A GB837360A GB 837360 A GB837360 A GB 837360A GB 5146/58 A GB5146/58 A GB 5146/58A GB 514658 A GB514658 A GB 514658A GB 837360 A GB837360 A GB 837360A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- hydroxy
- hydroxycinchoninic
- chloro
- amino
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title abstract 5
- LFLAICRWAWUQOF-UHFFFAOYSA-N 6-aminoquinolin-8-ol Chemical class N1=CC=CC2=CC(N)=CC(O)=C21 LFLAICRWAWUQOF-UHFFFAOYSA-N 0.000 title 1
- 230000008878 coupling Effects 0.000 title 1
- 238000010168 coupling process Methods 0.000 title 1
- 238000005859 coupling reaction Methods 0.000 title 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 5
- -1 6-substituted amino-8-hydroxycinchoninic acid Chemical class 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- WUJBIJXEOUIUCG-UHFFFAOYSA-N 3-amino-4-methyl-5-(tetradecanoylamino)benzenesulfonic acid Chemical compound C(CCCCCCCCCCCCC)(=O)NC1=CC(=CC(=C1C)N)S(=O)(=O)O WUJBIJXEOUIUCG-UHFFFAOYSA-N 0.000 abstract 1
- JUPVFHCFDMYITB-UHFFFAOYSA-N 6-[benzenesulfonyl(methyl)amino]-8-hydroxyquinoline-4-carboxylic acid Chemical compound CN(S(=O)(=O)C1=CC=CC=C1)C=1C=C2C(=CC=NC2=C(C1)O)C(=O)O JUPVFHCFDMYITB-UHFFFAOYSA-N 0.000 abstract 1
- HPPMSHYFVYKIJD-UHFFFAOYSA-N 6-anilino-8-hydroxy-2-methylquinoline-4-carboxylic acid Chemical compound C1(=CC=CC=C1)NC=1C=C2C(=CC(=NC2=C(C1)O)C)C(=O)O HPPMSHYFVYKIJD-UHFFFAOYSA-N 0.000 abstract 1
- IMUJTAIQEBHAMT-UHFFFAOYSA-N 6-bromoquinolin-8-ol Chemical compound C1=CN=C2C(O)=CC(Br)=CC2=C1 IMUJTAIQEBHAMT-UHFFFAOYSA-N 0.000 abstract 1
- DVZPTHVWIQDUHJ-UHFFFAOYSA-N 6-chloro-8-hydroxy-2-methylquinoline-4-carboxylic acid Chemical compound ClC=1C=C2C(=CC(=NC2=C(C1)O)C)C(=O)O DVZPTHVWIQDUHJ-UHFFFAOYSA-N 0.000 abstract 1
- NZPJBJIQYNZWTC-UHFFFAOYSA-N 6-chloro-8-hydroxy-2-phenylquinoline-4-carboxylic acid Chemical compound C1(=CC=CC=C1)C1=NC2=C(C=C(C=C2C(=C1)C(=O)O)Cl)O NZPJBJIQYNZWTC-UHFFFAOYSA-N 0.000 abstract 1
- ZEPFIXZXUFWKET-UHFFFAOYSA-N 6-chloro-8-hydroxyquinoline-4-carboxylic acid Chemical compound OC=1C=C(C=C2C(=CC=NC12)C(=O)O)Cl ZEPFIXZXUFWKET-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000843 powder Substances 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
- G03C7/3244—Couplers forming azinic dyes; Specific developers therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
6 - (b - Hydroxyethylamino) - 8 - hydroxy - 2-phenylcinchoninic acid is prepared by treating an aqueous sodium hydroxide solution of 2-phenyl - 6 - chloro - 8 - hydroxycinchoninic acid with ethanolamine, calcium carbonate and a trace of copper sulphate and copper bronze powder, and heating in an autoclave at 175 DEG C. Instead of ethanolamine, n-butylamine, b -carboxyethylamine, or b -sulphoethylamine may be used. Similarly, aniline, methylamine and p-anisidine are reacted respectively with a 6-halogen - 2 ; 3 - dimethyl - 8 - hydroxycinchoninic acid, 8 - hydroxy - 6 - chloro - cinchoninic acid and 6 - chloro - 8 - hydroxy - 2 - methylcinchoninic acid to give 6-substituted amino-8-hydroxycinchoninic acid derivatives. Similarly, ethylamine or b -hydroxyethylamine is reacted with 6-bromo-8-hydroxyquinoline to give a 6-substituted amino-8-hydroxy-quinoline. 3 - Tetradecanoylamido - 4 - methyl - 5 - [81-hydroxy - 61 - (N - methylbenzene - sulphonamido) cinchoninoylamido] benzene sulphonic acid is prepared by treating a mixture of 6-amino - 2 - myristoylamino - toluene - 4 - sulphonic acid and 6 - (N - methylbenzenesulphonamido) - 8 - hydroxycinchoninic acid in pyridine with phosphorus trichloride. N - (8 - Hydroxy - 2 - methyl - 4 - carboxy quinolinyl - 6 - acetanilide is prepared by acylating 6 - phenylamino - 8 - hydroxy - 2 - methylcinchoninic acid with acetyl chloride in pyridine or triethylamine. Specifications 633,760, 640,122, 644,863, 646,348, 647,638, 701,531 and 701,545 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US641481A US2886436A (en) | 1957-02-21 | 1957-02-21 | 5-amino-8-hydroxyquinolines as coupling components for azine dye images |
Publications (1)
Publication Number | Publication Date |
---|---|
GB837360A true GB837360A (en) | 1960-06-15 |
Family
ID=24572583
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5146/58A Expired GB837360A (en) | 1957-02-21 | 1958-02-17 | 6-amino-8-hydroxyquinolines as coupling components for azine dye images |
Country Status (3)
Country | Link |
---|---|
US (1) | US2886436A (en) |
DE (1) | DE1049701B (en) |
GB (1) | GB837360A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2257580B1 (en) * | 1974-01-10 | 1977-06-10 | Kodak Pathe | |
JPS56104333A (en) * | 1980-01-23 | 1981-08-20 | Fuji Photo Film Co Ltd | Color photographic sensitive material |
CA1285951C (en) * | 1985-10-28 | 1991-07-09 | Raj N. Misra | Naphthalenyl- and quinolinyl-amino substituted phenols |
US4847381A (en) * | 1987-08-31 | 1989-07-11 | American Cyanamid Company | 2-Phenyl-4-quinoline carboxylic acids |
DE4439329A1 (en) * | 1994-11-04 | 1996-05-09 | Agfa Gevaert Ag | New indolo [3,2-b] quinolines and their use in a color photographic development process |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2701766A (en) * | 1952-06-14 | 1955-02-08 | Gen Aniline & Film Corp | Developers for and method of producing phenazonium dyestuff images with p-dialkylaminoaniline developing agents |
-
0
- DE DENDAT1049701D patent/DE1049701B/de active Pending
-
1957
- 1957-02-21 US US641481A patent/US2886436A/en not_active Expired - Lifetime
-
1958
- 1958-02-17 GB GB5146/58A patent/GB837360A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
US2886436A (en) | 1959-05-12 |
DE1049701B (en) |
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