US2886436A - 5-amino-8-hydroxyquinolines as coupling components for azine dye images - Google Patents
5-amino-8-hydroxyquinolines as coupling components for azine dye images Download PDFInfo
- Publication number
- US2886436A US2886436A US641481A US64148157A US2886436A US 2886436 A US2886436 A US 2886436A US 641481 A US641481 A US 641481A US 64148157 A US64148157 A US 64148157A US 2886436 A US2886436 A US 2886436A
- Authority
- US
- United States
- Prior art keywords
- amino
- dye images
- azine dye
- acid
- hydroxyquinolines
- 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 - Lifetime
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 20
- 230000008878 coupling Effects 0.000 title description 3
- 238000010168 coupling process Methods 0.000 title description 3
- 238000005859 coupling reaction Methods 0.000 title description 3
- YDEUKNRKEYICTH-UHFFFAOYSA-N 5-aminoquinolin-8-ol Chemical class C1=CC=C2C(N)=CC=C(O)C2=N1 YDEUKNRKEYICTH-UHFFFAOYSA-N 0.000 title 1
- -1 SILVER HALIDE Chemical class 0.000 claims description 10
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- 239000000975 dye Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 150000001555 benzenes Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 230000008030 elimination Effects 0.000 description 6
- 238000003379 elimination reaction Methods 0.000 description 6
- 238000006798 ring closing metathesis reaction Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 description 2
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- LFLAICRWAWUQOF-UHFFFAOYSA-N 6-aminoquinolin-8-ol Chemical compound N1=CC=CC2=CC(N)=CC(O)=C21 LFLAICRWAWUQOF-UHFFFAOYSA-N 0.000 description 1
- IMUJTAIQEBHAMT-UHFFFAOYSA-N 6-bromoquinolin-8-ol Chemical compound C1=CN=C2C(O)=CC(Br)=CC2=C1 IMUJTAIQEBHAMT-UHFFFAOYSA-N 0.000 description 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 description 1
- 150000005639 6-haloquinolines Chemical class 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960002468 cinchophen Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 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
Definitions
- magenta azine dye images are of importance because of their greater brilliance and stability than the magenta quinonimine dye images obtained'in the usual fashion by coupling of a pyrazolone with the oxidation products-of a p-phenylenediamine.
- azine dye images be produced with the conventional p-phenylenediamine developers as may be seen from a reference to US. Patents 2,536,010 and 2,543,338.
- the color former which is used to produce the azine dyes is an aromatic phenol containing in the meta-position to the hydroxyl group, a sulfonyl amino group. After color forming development to produce the usual quinonimine dye, a ring closure is effected with elimination of the sulfonyl radical attached to the amino nitrogen atom.
- the color formers used are aromatic amines which contain in the meta-position to the amino group, an arylamino group or a cyano-or acylamino group.
- ring closure takes place through elimination of the substituents on the amino nitrogen atom, meta to the amino group.
- w-l r acyl such as acetyl, propionyl, butyryl, benzoyl and the like or sulfonyl such as methyl sulfonyl, ethyl sulfonyl, phenyl sulfonyland the like
- A is hydrogen, carboxyl or carbamino, i.e., -CONH or CONHR in which R is an alkyl radical as above or a sulfonated aromatic radical containingan aliphatic radical of at least five carbon atoms
- B is hydrogen, alkyl as above or an aromatic radical of the benzene series as above
- C is hydrogen, hydroxy, carboxy, alkyl as above, or an aromatic radical of the benzene series as above.
- color formers within the ambit of the above formula are the following:
- Compound 1 6-(p-methoxyphenylamino)-8-hydroxy-2-methy1cinchontuic aci 6-ethylamino-S-hydroxyquinoline All of the above compounds may be prepared by well known reactions. Typically, Compound 1 may be prepared as follows:
- the other six substituted 8-hydroxyquinolines specifically listed may be prepared by reacting the selected amine with a 6-haloquinoline in an autoclave at 150200- for 4 to 10 hours in the presence of a copper catalyst.
- n-butylamine is reacted in this way with 6-chlo1'o- 8- hydroxy-Z-phenylcinchoninic acid or p-anisidine with 6- chloro-S-hydroxy-Z-methylcinchoninic acid to yield Comat pounds 6 and 8 respectively.
- ethylamine is reacted with 6-bromo-8-hydroxyquinoline to yield Compound 9 and methylamine reacted with 6-chloro- S-hydroxycinchoninic acid toyi eld Compound 7.
- a conversion of the secondary amine to amides or sulfonarnides is effected by reaction of the amine with an appropriate carbonylchloride in the presence of an acid binding agent such as pyridine or triethylamine.
- the product is then isolated by the removal of the solvent at reduced pressure and acidification of the residue after dilution with water.
- the 4-carboxamides, as in Compound 3 are prepared by treatment of a mixture of 6-amino-2-myristoylaminotoluene-4-sulfonic acid and 6-(methylaminobenzenesulfonamide)-8-hydroxy-2-methylcinchoninic acid in pyridine solution with one-half mole of phosphorous trichloride.
- the azine dye image is produced from the originally formed quinonimine through elimination of the elements of acyl or sulfonyl from the amino group ortho to the intermediate azomethine coupled position in the quinoline nucleus and elimination of hydrogen from the benzene, ring ortho to the primary amino group originally present in the developer molecule.
- Such ring closure is schematically represented by the following equation:
- a color developing solution is prepared as follows:
- Compound 1 0.1 gram was dissolved in 5% sodium carbonate solution (5 mls.) and the solution was made up to 5 0 mls. with a portion of the aforesaid color developer solution.
- a strip of exposed positive film is agitated in this solution for 5 to 10 minutes.
- the film on which a green azomethine dye is orginally produced is bleached in ferricyauide and fixed in acid hypo. On treatment with the acid hypo, the green azomethine dye converts to a brilliant magenta azine dye.
- any of the compounds listed above may be utilized for our purpose.
- the couplers are to be employed in the emulsion, they should contain a non-difiusing group, preferably an alkyl chain of at least 1-0 carbon atoms as per Compound 3. If, on the other hand, they are to be used in the developer, they should not possess groups which render them nondifiusing in the emulsion.
- W is selected from the class consisting of alkyl, hydroxyalkyl, carboxyalkyl, sulfoalkyl, and aryl of the benzene series
- Y is selected from the class consisting of hydrogen, acyl and sulfonyl groups.
- A is selected from the class consisting of hydrogen, carboxyl and carbamino groups
- B is selected from the class consisting of hydrogen, alkyl and aryl of the benzene series
- C is selected from the class consisting of hydrogen, hydroxy, carboxy, alkyl and aryl of the benzene series.
- W is selected from the class consisting of alkyl, hydroxyalkyl, carboxyalkyl, sulfoalkyl and aryl of the benzene series
- Y is selected from the class consisting of hydrogen, acyl and sulfonyl groups
- A is selected from the class consisting of hydrogen, carboxyl and carbamino groups
- B is selected from the class consisting of hydrogen, alkyl and aryl of the benzene series
- C is selected from the class consisting of hydrogen, hydroxy, carboxy, alkyl and aryl of the benzene series.
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)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DENDAT1049701D DE1049701B (es) | 1957-02-21 | ||
| US641481A US2886436A (en) | 1957-02-21 | 1957-02-21 | 5-amino-8-hydroxyquinolines as coupling components for azine dye images |
| GB5146/58A GB837360A (en) | 1957-02-21 | 1958-02-17 | 6-amino-8-hydroxyquinolines as coupling components for azine dye images |
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 |
|---|---|
| US2886436A true US2886436A (en) | 1959-05-12 |
Family
ID=24572583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US641481A Expired - Lifetime US2886436A (en) | 1957-02-21 | 1957-02-21 | 5-amino-8-hydroxyquinolines as coupling components for azine dye images |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2886436A (es) |
| DE (1) | DE1049701B (es) |
| GB (1) | GB837360A (es) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970454A (en) * | 1974-01-10 | 1976-07-20 | Eastman Kodak Company | Photographic developing agents |
| US4327173A (en) * | 1980-01-23 | 1982-04-27 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4814454A (en) * | 1985-10-28 | 1989-03-21 | E. R. Squibb & Sons, Inc. | Quinoline compounds and compositions thereof |
| US4847381A (en) * | 1987-08-31 | 1989-07-11 | American Cyanamid Company | 2-Phenyl-4-quinoline carboxylic acids |
| US5573892A (en) * | 1994-11-04 | 1996-11-12 | Agfa-Gevaert Ag | Use of Yellow couplers of the indolo [3,2-B] guinoline type in a colo ur photographic development process |
Citations (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
Patent Citations (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 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970454A (en) * | 1974-01-10 | 1976-07-20 | Eastman Kodak Company | Photographic developing agents |
| US4327173A (en) * | 1980-01-23 | 1982-04-27 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4814454A (en) * | 1985-10-28 | 1989-03-21 | E. R. Squibb & Sons, Inc. | Quinoline compounds and compositions thereof |
| US4847381A (en) * | 1987-08-31 | 1989-07-11 | American Cyanamid Company | 2-Phenyl-4-quinoline carboxylic acids |
| US5573892A (en) * | 1994-11-04 | 1996-11-12 | Agfa-Gevaert Ag | Use of Yellow couplers of the indolo [3,2-B] guinoline type in a colo ur photographic development process |
Also Published As
| Publication number | Publication date |
|---|---|
| GB837360A (en) | 1960-06-15 |
| DE1049701B (es) |
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