GB1003783A - Improvements in or relating to photographic development and developing compositions - Google Patents
Improvements in or relating to photographic development and developing compositionsInfo
- Publication number
- GB1003783A GB1003783A GB24852/61A GB2485261A GB1003783A GB 1003783 A GB1003783 A GB 1003783A GB 24852/61 A GB24852/61 A GB 24852/61A GB 2485261 A GB2485261 A GB 2485261A GB 1003783 A GB1003783 A GB 1003783A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyphenyl
- pyrrolidine
- prepared
- hydroxy
- ethyl
- 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
- 239000000203 mixture Substances 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- -1 3- chloro - 4 hydroxyphenyl Chemical group 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- YXZLIZVQQRNTIL-UHFFFAOYSA-N N(C(=O)C)C=1C=C(C=CC1OC)N1CCCC1 Chemical compound N(C(=O)C)C=1C=C(C=CC1OC)N1CCCC1 YXZLIZVQQRNTIL-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- CTJSPUFGQNVJJP-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-6-ol Chemical compound N1CCCC2=CC(O)=CC=C21 CTJSPUFGQNVJJP-UHFFFAOYSA-N 0.000 abstract 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- IOYCEITYZXFIPX-UHFFFAOYSA-N 4-(6-hydroxy-3,4-dihydro-2H-quinolin-1-yl)butane-1-sulfonic acid Chemical compound S(=O)(=O)(O)CCCCN1CCCC2=CC(=CC=C12)O IOYCEITYZXFIPX-UHFFFAOYSA-N 0.000 abstract 1
- AOXXBEMAOZDIQO-UHFFFAOYSA-N 4-pyrrolidin-1-ylphenol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1N1CCCC1 AOXXBEMAOZDIQO-UHFFFAOYSA-N 0.000 abstract 1
- NXUFMUVAMSORHO-UHFFFAOYSA-N Br.Br.NC=1C=C(C=CC1O)N1CCCC1 Chemical compound Br.Br.NC=1C=C(C=CC1O)N1CCCC1 NXUFMUVAMSORHO-UHFFFAOYSA-N 0.000 abstract 1
- QCQCGAXUJKOQFK-UHFFFAOYSA-N Cl.C(C)N1CCCC2=CC(=CC=C12)O Chemical compound Cl.C(C)N1CCCC2=CC(=CC=C12)O QCQCGAXUJKOQFK-UHFFFAOYSA-N 0.000 abstract 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- BTNWTSYUNCUTSP-UHFFFAOYSA-N n'-(4-methoxyphenyl)acetohydrazide Chemical compound COC1=CC=C(NNC(C)=O)C=C1 BTNWTSYUNCUTSP-UHFFFAOYSA-N 0.000 abstract 1
- BXVCFLARGCBLEP-UHFFFAOYSA-N n-(2-bromoethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCBr BXVCFLARGCBLEP-UHFFFAOYSA-N 0.000 abstract 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- C07D215/20—Oxygen atoms
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/30—Developers
- G03C5/3021—Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring
-
- 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
- G03C8/02—Photosensitive materials characterised by the image-forming section
- G03C8/04—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of inorganic or organo-metallic compounds derived from photosensitive noble metals
- G03C8/06—Silver salt diffusion transfer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1 - (4 - Hydroxyphenyl) - pyrrolidine hydrochloride is prepared by hydrolysis of the 1-p-methoxy phenyl compound with hydrobromic acid. The reaction mixture is neutralized with sodium bicarbonate, and the free base converted to the hydrochloride by passing hydrogen chloride gas through an ethereal solution. 1-(3-Acetamino - 4 - methoxyphenyl) - pyrrolidine is similarly hydrolysed to 1 - (3 - amino - 4 - hydroxyphenyl) - pyrrolidine dihydrobromide. The free base of this is obtained using sodium bicarbonate and this is then reacted with methane sulphonyl chloride or acetic anhydride to yield respectively 1 - (3 - methylsulphonylamino - or 3 - acetylamino - 4 - hydroxyphenyl)- pyrrolidine. 1 - (3 - Acetamino - 4 - methoxyphenyl)-pyrrolidine is prepared by reacting 3 acetylamino-4-methoxyaniline with 1,4-dibromobutane in the presence of sodium carbonate. Pyrrolidine substituted in the 1-position by 3- chloro - 4 hydroxyphenyl, 3-5 - dimethyl - 4-hydroxyphenyl, and 3 - methoxy - 4 - hydroxyphenyl groups are similarly prepared from the appropriate aminophenols and 1; 4-dibromobutane. 1 - Ethyl - 6 - hydroxy - 1,2,3,4 - tetrahydroquinoline hydrochloride is prepared by refluxing 6 - hydroxy - 1,2,3,4 - tetrahydroquinoline with ethyl bromide and potassium carbonate in ethanol and acidifying the product with alcoholic hydrochloric acid. The corresponding 1 - b - methylsulphonylamino - ethyl and 1 - b - hydroxy-ethyl compounds are similarly prepared from 1 - bromo - 2 - methylsulphonamidoethane and b -bromo-ethanol respectively, the latter reaction taking place in the presence of potassium hydroxide and benzyl chloride. The 1 - (4 - sulphobutyl) - 6 - hydroxy - 1,2,3,4 - tetrahydroquinoline is prepared from the corresponding base and butane sultone.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24852/61A GB1003783A (en) | 1961-07-10 | 1961-07-10 | Improvements in or relating to photographic development and developing compositions |
| DEG35415A DE1284298B (en) | 1961-07-10 | 1962-07-07 | Process for developing an exposed light-sensitive silver halide emulsion |
| US208572A US3265499A (en) | 1961-07-10 | 1962-07-09 | Photographic developing compositions |
| FR903514A FR1332260A (en) | 1961-07-10 | 1962-07-10 | Revealing photographic compositions |
| BE619971A BE619971A (en) | 1961-07-10 | 1962-07-10 | Photographic development compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24852/61A GB1003783A (en) | 1961-07-10 | 1961-07-10 | Improvements in or relating to photographic development and developing compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1003783A true GB1003783A (en) | 1965-09-08 |
Family
ID=10218266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24852/61A Expired GB1003783A (en) | 1961-07-10 | 1961-07-10 | Improvements in or relating to photographic development and developing compositions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3265499A (en) |
| BE (1) | BE619971A (en) |
| DE (1) | DE1284298B (en) |
| GB (1) | GB1003783A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4798779A (en) * | 1986-01-30 | 1989-01-17 | Fuji Photo Film Co., Ltd. | Process for forming an image by silver salt diffusion transfer |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3379528A (en) * | 1964-07-17 | 1968-04-23 | Eastman Kodak Co | Activator solution rejuvenation |
| BE757902A (en) * | 1969-10-27 | 1971-04-23 | Agfa Gevaert Nv | METHOD OF PHOTOGRAPHIC DEVELOPMENT |
| JPS4943333B1 (en) * | 1970-10-27 | 1974-11-20 | ||
| EP0512496B1 (en) * | 1991-05-10 | 1995-12-20 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| JPH07128819A (en) * | 1993-10-28 | 1995-05-19 | Fuji Photo Film Co Ltd | Silver halide color photographic sensitive material and its processing method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072480A (en) * | 1959-04-10 | 1963-01-08 | Eastman Kodak Co | Photographic diffusion transfer process |
| FR1283420A (en) * | 1960-02-19 | 1962-02-02 | Ilford Ltd | New compositions of photographic developers and their preparation |
-
1961
- 1961-07-10 GB GB24852/61A patent/GB1003783A/en not_active Expired
-
1962
- 1962-07-07 DE DEG35415A patent/DE1284298B/en active Pending
- 1962-07-09 US US208572A patent/US3265499A/en not_active Expired - Lifetime
- 1962-07-10 BE BE619971A patent/BE619971A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4798779A (en) * | 1986-01-30 | 1989-01-17 | Fuji Photo Film Co., Ltd. | Process for forming an image by silver salt diffusion transfer |
Also Published As
| Publication number | Publication date |
|---|---|
| BE619971A (en) | 1962-11-05 |
| DE1284298B (en) | 1968-11-28 |
| US3265499A (en) | 1966-08-09 |
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