DE69327405T2 - Verbindungen zur Herstellung eines photographischen Magentakupplers - Google Patents
Verbindungen zur Herstellung eines photographischen MagentakupplersInfo
- Publication number
- DE69327405T2 DE69327405T2 DE69327405T DE69327405T DE69327405T2 DE 69327405 T2 DE69327405 T2 DE 69327405T2 DE 69327405 T DE69327405 T DE 69327405T DE 69327405 T DE69327405 T DE 69327405T DE 69327405 T2 DE69327405 T2 DE 69327405T2
- Authority
- DE
- Germany
- Prior art keywords
- added
- mixture
- compound
- stirred
- compounds
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000013078 crystal Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- BXUURYQQDJGIGA-UHFFFAOYSA-N N1C=NN2N=CC=C21 Chemical compound N1C=NN2N=CC=C21 BXUURYQQDJGIGA-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
- ZHBXGHWSVIBUCQ-UHFFFAOYSA-N 5-tert-butyl-1h-pyrazol-3-amine Chemical compound CC(C)(C)C1=CC(N)=NN1 ZHBXGHWSVIBUCQ-UHFFFAOYSA-N 0.000 description 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NOOCRARVXLNZGF-UHFFFAOYSA-N 2-octoxy-5-(2,4,4-trimethylpentan-2-yl)benzenesulfonyl chloride Chemical compound CCCCCCCCOC1=CC=C(C(C)(C)CC(C)(C)C)C=C1S(Cl)(=O)=O NOOCRARVXLNZGF-UHFFFAOYSA-N 0.000 description 1
- UFFAAOZGRVHEFM-UHFFFAOYSA-N 2-octyl-5-(2,4,4-trimethylpentan-2-yl)benzenesulfonyl chloride Chemical compound CCCCCCCCC1=CC=C(C(C)(C)CC(C)(C)C)C=C1S(Cl)(=O)=O UFFAAOZGRVHEFM-UHFFFAOYSA-N 0.000 description 1
- MXZMACXOMZKYHJ-UHFFFAOYSA-N 4,4-dimethyl-3-oxopentanenitrile Chemical compound CC(C)(C)C(=O)CC#N MXZMACXOMZKYHJ-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
- G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
- G03C7/30529—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution having the coupling site in rings of cyclic compounds
-
- 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
- G03C7/381—Heterocyclic compounds
- G03C7/382—Heterocyclic compounds with two heterocyclic rings
- G03C7/3825—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms
- G03C7/3835—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms four nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15740592 | 1992-05-26 | ||
| JP4234120A JP2670943B2 (ja) | 1992-05-26 | 1992-08-11 | 写真用カプラー及びハロゲン化銀カラー写真感光材料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69327405D1 DE69327405D1 (de) | 2000-01-27 |
| DE69327405T2 true DE69327405T2 (de) | 2000-05-04 |
Family
ID=26484874
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69309537T Expired - Lifetime DE69309537T2 (de) | 1992-05-26 | 1993-05-25 | Photographischer Kuppler und farbphotographisches Silberhalogenidmaterial |
| DE69327405T Expired - Lifetime DE69327405T2 (de) | 1992-05-26 | 1993-05-25 | Verbindungen zur Herstellung eines photographischen Magentakupplers |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69309537T Expired - Lifetime DE69309537T2 (de) | 1992-05-26 | 1993-05-25 | Photographischer Kuppler und farbphotographisches Silberhalogenidmaterial |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US5451501A (OSRAM) |
| EP (2) | EP0571959B1 (OSRAM) |
| JP (1) | JP2670943B2 (OSRAM) |
| DE (2) | DE69309537T2 (OSRAM) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5368998A (en) * | 1993-01-14 | 1994-11-29 | Konica Corporation | Silver halide color photographic light sensitive material |
| JPH0720617A (ja) * | 1993-07-02 | 1995-01-24 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JP3026244B2 (ja) * | 1993-10-19 | 2000-03-27 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JP3515602B2 (ja) * | 1994-01-27 | 2004-04-05 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料及びカラー画像形成方法 |
| JP3388877B2 (ja) * | 1994-05-10 | 2003-03-24 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| US5578437A (en) * | 1994-05-11 | 1996-11-26 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US5597679A (en) * | 1994-05-11 | 1997-01-28 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0697623B1 (en) * | 1994-08-17 | 1998-03-25 | Fuji Photo Film Co., Ltd. | Silver halide photographic material containing pyrazolone-pentamethine oxonol dye |
| JPH08202001A (ja) | 1995-01-30 | 1996-08-09 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| DE19819830A1 (de) * | 1998-05-04 | 1999-11-11 | Agfa Gevaert Ag | Farbfotografisches Kopiermaterial |
| FR2782081B1 (fr) * | 1998-08-04 | 2001-07-27 | Isochem Sa | Procede de preparation de carboxamides-oximes |
| US6143485A (en) * | 1998-12-23 | 2000-11-07 | Eastman Kodak Company | Pyrazolotriazle dye-forming photographic coupler |
| JP4156176B2 (ja) | 2000-06-09 | 2008-09-24 | 富士フイルム株式会社 | カプラーおよびハロゲン化銀カラー写真感光材料 |
| US6995273B2 (en) | 2000-06-09 | 2006-02-07 | Fuji Photo Film Co., Ltd. | 1H-pyrazolo[1,5-b]-1,2,4-triazole compound, coupler and silver halide color photographic light-sensitive material |
| US6946562B2 (en) * | 2001-12-12 | 2005-09-20 | Eastman Kodak Company | Synthesis of peptoid substituted azole compounds |
| US6514679B1 (en) | 2001-12-12 | 2003-02-04 | Eastman Kodak Company | Imaging materials containing peptoid substituted azole couplers |
| US6916601B2 (en) * | 2001-12-28 | 2005-07-12 | Fuji Photo Film Co., Ltd. | Image-forming method using a silver halide color photographic light-sensitive material, and silver halide color photographic light-sensitive material |
| DE10230981A1 (de) | 2002-07-10 | 2004-01-29 | Agfa-Gevaert Ag | Farbfotografisches Kopiermaterial |
| DE10230980A1 (de) | 2002-07-10 | 2004-01-29 | Agfa-Gevaert Ag | Farbfotografisches Silberhalogenidmaterial |
| DE10230978A1 (de) | 2002-07-10 | 2004-01-29 | Agfa-Gevaert Ag | Farbfotografisches Kopiermaterial |
| DE10230984A1 (de) * | 2002-07-10 | 2004-01-29 | Agfa-Gevaert Ag | Farbfotografisches Kopiermaterial |
| CN1512264B (zh) * | 2002-12-27 | 2010-05-26 | 富士胶片株式会社 | 卤化银彩色照相感光材料 |
| JP4369876B2 (ja) | 2004-03-23 | 2009-11-25 | 富士フイルム株式会社 | ハロゲン化銀感光材料および熱現像感光材料 |
| DE102004031899A1 (de) * | 2004-07-01 | 2006-01-26 | Agfa-Gevaert Ag | Silberhalogenidmaterial |
| US7687229B2 (en) | 2004-08-24 | 2010-03-30 | Fujifilm Corporation | Silver halide color photographic light-sensitive material and image forming method |
| US20060057512A1 (en) | 2004-09-14 | 2006-03-16 | Fuji Photo Film Co., Ltd. | Photothermographic material |
| JP2007051193A (ja) | 2005-08-17 | 2007-03-01 | Fujifilm Corp | インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び、平版印刷版 |
| JP5106285B2 (ja) | 2008-07-16 | 2012-12-26 | 富士フイルム株式会社 | 光硬化性組成物、インク組成物、及び該インク組成物を用いたインクジェット記録方法 |
| JP2010077228A (ja) | 2008-09-25 | 2010-04-08 | Fujifilm Corp | インク組成物、インクジェット記録方法、及び、印刷物 |
| JP2010256908A (ja) | 2010-05-07 | 2010-11-11 | Fujifilm Corp | 映画用ハロゲン化銀写真感光材料 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4621046A (en) * | 1983-03-18 | 1986-11-04 | Fuji Photo Film Co., Ltd. | Pyrazolo(1,5-B)-1,2,4-triazole derivatives |
| JPS59171956A (ja) * | 1983-03-18 | 1984-09-28 | Fuji Photo Film Co Ltd | カラ−画像形成方法 |
| JPS6165245A (ja) * | 1984-09-06 | 1986-04-03 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| US4639415A (en) * | 1984-09-17 | 1987-01-27 | Konishiroku Photo Industry Co., Ltd. | Silver halide color photographic material containing a magenta color image-forming coupler |
| AU590557B2 (en) * | 1985-04-25 | 1989-11-09 | Konishiroku Photo Industry Co., Ltd. | Processing method of light-sensitive silver halide color photographic material |
| JPS61249053A (ja) * | 1985-04-26 | 1986-11-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| DE3624544C2 (de) * | 1986-07-19 | 1996-02-01 | Agfa Gevaert Ag | Farbfotografisches Aufzeichnungsmaterial mit einem Farbkuppler vom Pyrazoloazol-Typ |
| US4873183A (en) * | 1986-11-25 | 1989-10-10 | Konica Corporation | Silver halide color photographic light-sensitive material containing pyrazoloazole type cyan coupler |
| JPH01250955A (ja) * | 1987-12-09 | 1989-10-05 | Fuji Photo Film Co Ltd | カラー写真感光材料 |
| JPH0662625B2 (ja) * | 1988-03-15 | 1994-08-17 | 富士写真フイルム株式会社 | １Ｈ−ピラゾロ〔５，１−ｃ〕−１，２，４−トリアゾール系化合物の製造方法 |
| JPH02201358A (ja) * | 1989-01-30 | 1990-08-09 | Konica Corp | 新規なシアンカプラーを含有するハロゲン化銀カラー写真感光材料 |
| JPH01302249A (ja) * | 1989-03-02 | 1989-12-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JP2631145B2 (ja) * | 1989-07-18 | 1997-07-16 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料および該感材を用いて得られたカラー写真 |
| JPH0351846A (ja) * | 1989-07-20 | 1991-03-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JPH089620B2 (ja) * | 1990-01-23 | 1996-01-31 | 富士写真フイルム株式会社 | １ｈ―ピラゾロ〔５，１―ｃ〕―１，２，４―トリアゾール化合物の製造方法 |
| EP0476949A1 (en) * | 1990-09-19 | 1992-03-25 | Konica Corporation | Silver halide color photographic light sensitive material |
| JPH0580473A (ja) * | 1991-09-18 | 1993-04-02 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| JPH05142727A (ja) * | 1991-11-19 | 1993-06-11 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JP2893100B2 (ja) * | 1991-11-27 | 1999-05-17 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JP2952540B2 (ja) * | 1992-03-04 | 1999-09-27 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料およびこれを用いたカラー画像形成法 |
-
1992
- 1992-08-11 JP JP4234120A patent/JP2670943B2/ja not_active Expired - Fee Related
-
1993
- 1993-05-25 EP EP93108447A patent/EP0571959B1/en not_active Expired - Lifetime
- 1993-05-25 DE DE69309537T patent/DE69309537T2/de not_active Expired - Lifetime
- 1993-05-25 DE DE69327405T patent/DE69327405T2/de not_active Expired - Lifetime
- 1993-05-25 EP EP95112304A patent/EP0688774B1/en not_active Expired - Lifetime
- 1993-05-26 US US08/067,111 patent/US5451501A/en not_active Expired - Lifetime
-
1995
- 1995-06-06 US US08/467,833 patent/US5532377A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0643611A (ja) | 1994-02-18 |
| US5451501A (en) | 1995-09-19 |
| DE69309537D1 (de) | 1997-05-15 |
| EP0688774B1 (en) | 1999-12-22 |
| EP0571959A2 (en) | 1993-12-01 |
| DE69327405D1 (de) | 2000-01-27 |
| JP2670943B2 (ja) | 1997-10-29 |
| DE69309537T2 (de) | 1997-07-24 |
| EP0688774A1 (en) | 1995-12-27 |
| US5532377A (en) | 1996-07-02 |
| EP0571959B1 (en) | 1997-04-09 |
| EP0571959A3 (OSRAM) | 1994-03-16 |
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| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: FUJIFILM CORP., TOKIO/TOKYO, JP |