GB1069061A - N-aminophenyl-phthalimido derivatives and their use in photographic colour developing - Google Patents
N-aminophenyl-phthalimido derivatives and their use in photographic colour developingInfo
- Publication number
- GB1069061A GB1069061A GB579665A GB579665A GB1069061A GB 1069061 A GB1069061 A GB 1069061A GB 579665 A GB579665 A GB 579665A GB 579665 A GB579665 A GB 579665A GB 1069061 A GB1069061 A GB 1069061A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- prepared
- potassium
- formula
- sulphonamide
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229940124530 sulfonamide Drugs 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 abstract 1
- CJONVIXTBSYUTK-UHFFFAOYSA-N C1(C=2C(C(=O)O1)=CC=CC2)=O.[K].[K] Chemical compound C1(C=2C(C(=O)O1)=CC=CC2)=O.[K].[K] CJONVIXTBSYUTK-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- WZJDLKBZUBHBGM-UHFFFAOYSA-N [K].C1(C=2C(C(=O)O1)=CC=CC2)=O Chemical compound [K].C1(C=2C(C(=O)O1)=CC=CC2)=O WZJDLKBZUBHBGM-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- MINVSWONZWKMDC-UHFFFAOYSA-L mercuriooxysulfonyloxymercury Chemical compound [Hg+].[Hg+].[O-]S([O-])(=O)=O MINVSWONZWKMDC-UHFFFAOYSA-L 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- DFOLZSTWYAQVDC-UHFFFAOYSA-N phthalic acid;potassium Chemical compound [K].[K].OC(=O)C1=CC=CC=C1C(O)=O DFOLZSTWYAQVDC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/42—Developers or their precursors
-
- 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
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
- G03C7/4136—Developers p-Phenylenediamine or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Indole Compounds (AREA)
Abstract
The invention comprises compounds of the general Formula 1 <FORM:1069061/C2/1> wherein R1 and R2 are substituted or unsubstituted alkyl radicals or R1 and R2 are joined together to form with the nitrogen atom a heterocyclic ring; X is hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, amino or substituted amino; 7 is a carboxylic or a sulphonic acid group or a salt of either of these; and Z is an electronegative group. They may be prepared by condensing an amine of the Formula 2 <FORM:1069061/C2/2> with a compound of the Formula 3 <FORM:1069061/C2/3> at a temperature above 100 DEG C. Compound of the Formula 4 <FORM:1069061/C2/4> may also be prepared by condensing an amin of Formula 2 with pyromellitic dianhydride at ambient temperature to produce a compound of the Formula 5 <FORM:1069061/C2/5> and refluxing said product in glacial acetic acid. Sodium - potassium - 5 - sulpho - trimellitic anhydride is prepared by refluxing a mixture of sodium - potassium - 5 - sulphotrimellitic acid and acetic anhydride. Di - potassium - phthalic anhydride - 3 : 5-disulphonate is prepared by heating di-potassium phthalic acid-3 : 5-disulphonate. Di - potassium - phthalic acid - 3 : 5 - disulphonate is prepared by heating phthalic anhydride and mercurous sulphate whilst bubbling sulphur trioxide through the molten mass and treating the reaction product with potassium hydroxide. Potassium - phthalic anhydride - 4 - sulphonamide-5-carboxylate is prepared by refluxing monopotassium trimellitic acid-4-sulphonamide with acetic anhydride. Monopotassium trimellitic acid-4-sulphonamide is prepared by adding potassium permanganate to a mixture of 4-m-xylic acid-5-sulphonamide, sodium hydroxide and water. 4 - m - Xylic acid - 5 - sulphonamide is prepared by reacting 4-m-xylic acid with chlorosulphonic acid to form 4-m-xylic acid-5-sulphonyl chloride and reacting this chloride with ammonia.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB579665A GB1069061A (en) | 1965-02-10 | 1965-02-10 | N-aminophenyl-phthalimido derivatives and their use in photographic colour developing |
| DE19661547981 DE1547981A1 (en) | 1965-02-10 | 1966-02-08 | Color development process |
| FR48952A FR1467707A (en) | 1965-02-10 | 1966-02-09 | Developers for color photography |
| CH181866A CH466038A (en) | 1965-02-10 | 1966-02-09 | Color development process |
| BE676313D BE676313A (en) | 1965-02-10 | 1966-02-10 | |
| NL6601717A NL6601717A (en) | 1965-02-10 | 1966-02-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB579665A GB1069061A (en) | 1965-02-10 | 1965-02-10 | N-aminophenyl-phthalimido derivatives and their use in photographic colour developing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1069061A true GB1069061A (en) | 1967-05-17 |
Family
ID=9802786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB579665A Expired GB1069061A (en) | 1965-02-10 | 1965-02-10 | N-aminophenyl-phthalimido derivatives and their use in photographic colour developing |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE676313A (en) |
| CH (1) | CH466038A (en) |
| DE (1) | DE1547981A1 (en) |
| GB (1) | GB1069061A (en) |
| NL (1) | NL6601717A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244857A (en) * | 1979-08-30 | 1981-01-13 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Curing agent for polyepoxides and epoxy resins and composites cured therewith |
| US4935523A (en) * | 1985-09-30 | 1990-06-19 | The Boeing Company | Crosslinking imidophenylamines |
| US4985568A (en) * | 1985-09-30 | 1991-01-15 | The Boeing Company | Method of making crosslinking imidophenylamines |
| US5506060A (en) | 1981-11-13 | 1996-04-09 | The Boeing Company | Method for making multidimensional ether or ester oligomers |
| US5554769A (en) | 1987-09-03 | 1996-09-10 | The Boeing Company | Extended end cap monomer for making advanced composites |
| US5573854A (en) | 1981-11-13 | 1996-11-12 | The Boeing Company | Composites made from multidimensional oligomers |
| US5587105A (en) | 1988-03-15 | 1996-12-24 | Sheppard; Clyde H. | Methods for making liquid molding compounds using diamines and dicyanates |
| US5602226A (en) | 1985-04-23 | 1997-02-11 | The Boeing Company | Method of making multidimensional polyesters |
| US5610317A (en) | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| US5667945A (en) * | 1995-02-21 | 1997-09-16 | Fuji Photo Film Co., Ltd. | Color developing agent, silver halide photographic light-sensitive material and image forming method |
| US5705574A (en) | 1983-09-27 | 1998-01-06 | The Boeing Company | Method for making a polyimide blend |
| US5739256A (en) | 1985-04-23 | 1998-04-14 | The Boeing Company | Method for making multidimensional polyester oligomers |
| US5756275A (en) * | 1995-11-30 | 1998-05-26 | Fuji Photo Film Co., Ltd. | Color-developing agent, silver halide photographic light-sensitive material and image-forming method |
| US5780210A (en) * | 1995-02-15 | 1998-07-14 | Fuji Photo Film Co., Ltd. | Color developing agent, silver halide photographic light-sensitive material and image forming method |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| US5874203A (en) * | 1995-11-30 | 1999-02-23 | Fuji Photo Film, Co., Ltd. | Color-developing agent, silver halide photographic light-sensitive material and image-forming method |
| US5889163A (en) * | 1995-11-30 | 1999-03-30 | Fuji Photo Film Co., Ltd. | Method for producing azo dye compounds |
| US6103458A (en) * | 1996-08-02 | 2000-08-15 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide color photographic light-sensitive material |
-
1965
- 1965-02-10 GB GB579665A patent/GB1069061A/en not_active Expired
-
1966
- 1966-02-08 DE DE19661547981 patent/DE1547981A1/en active Pending
- 1966-02-09 CH CH181866A patent/CH466038A/en unknown
- 1966-02-10 NL NL6601717A patent/NL6601717A/xx unknown
- 1966-02-10 BE BE676313D patent/BE676313A/xx unknown
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244857A (en) * | 1979-08-30 | 1981-01-13 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Curing agent for polyepoxides and epoxy resins and composites cured therewith |
| US5506060A (en) | 1981-11-13 | 1996-04-09 | The Boeing Company | Method for making multidimensional ether or ester oligomers |
| US5573854A (en) | 1981-11-13 | 1996-11-12 | The Boeing Company | Composites made from multidimensional oligomers |
| US5705574A (en) | 1983-09-27 | 1998-01-06 | The Boeing Company | Method for making a polyimide blend |
| US5739256A (en) | 1985-04-23 | 1998-04-14 | The Boeing Company | Method for making multidimensional polyester oligomers |
| US6583255B1 (en) | 1985-04-23 | 2003-06-24 | The Boeing Company | Polyester oligomer |
| US5602226A (en) | 1985-04-23 | 1997-02-11 | The Boeing Company | Method of making multidimensional polyesters |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| US5610317A (en) | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| US4935523A (en) * | 1985-09-30 | 1990-06-19 | The Boeing Company | Crosslinking imidophenylamines |
| US4985568A (en) * | 1985-09-30 | 1991-01-15 | The Boeing Company | Method of making crosslinking imidophenylamines |
| US5554769A (en) | 1987-09-03 | 1996-09-10 | The Boeing Company | Extended end cap monomer for making advanced composites |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| US5587105A (en) | 1988-03-15 | 1996-12-24 | Sheppard; Clyde H. | Methods for making liquid molding compounds using diamines and dicyanates |
| US5780210A (en) * | 1995-02-15 | 1998-07-14 | Fuji Photo Film Co., Ltd. | Color developing agent, silver halide photographic light-sensitive material and image forming method |
| US5667945A (en) * | 1995-02-21 | 1997-09-16 | Fuji Photo Film Co., Ltd. | Color developing agent, silver halide photographic light-sensitive material and image forming method |
| US5756275A (en) * | 1995-11-30 | 1998-05-26 | Fuji Photo Film Co., Ltd. | Color-developing agent, silver halide photographic light-sensitive material and image-forming method |
| US5874203A (en) * | 1995-11-30 | 1999-02-23 | Fuji Photo Film, Co., Ltd. | Color-developing agent, silver halide photographic light-sensitive material and image-forming method |
| US5889163A (en) * | 1995-11-30 | 1999-03-30 | Fuji Photo Film Co., Ltd. | Method for producing azo dye compounds |
| US6103458A (en) * | 1996-08-02 | 2000-08-15 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide color photographic light-sensitive material |
Also Published As
| Publication number | Publication date |
|---|---|
| CH466038A (en) | 1968-11-30 |
| BE676313A (en) | 1966-06-16 |
| DE1547981A1 (en) | 1970-02-12 |
| NL6601717A (en) | 1966-08-11 |
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