US2753265A - Photographic developing compositions - Google Patents
Photographic developing compositions Download PDFInfo
- Publication number
- US2753265A US2753265A US528547A US52854755A US2753265A US 2753265 A US2753265 A US 2753265A US 528547 A US528547 A US 528547A US 52854755 A US52854755 A US 52854755A US 2753265 A US2753265 A US 2753265A
- Authority
- US
- United States
- Prior art keywords
- pyrazolidone
- acetic acid
- amino acetic
- phenyl
- photographic
- 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
- 239000000203 mixture Substances 0.000 title claims description 25
- WRUZLCLJULHLEY-UHFFFAOYSA-N N-(p-hydroxyphenyl)glycine Chemical compound OC(=O)CNC1=CC=C(O)C=C1 WRUZLCLJULHLEY-UHFFFAOYSA-N 0.000 claims description 21
- 239000012670 alkaline solution Substances 0.000 claims description 17
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical compound O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 description 16
- 239000003513 alkali Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004285 Potassium sulphite Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 3
- 235000019252 potassium sulphite Nutrition 0.000 description 3
- FJWJYHHBUMICTP-UHFFFAOYSA-N 4,4-dimethylpyrazolidin-3-one Chemical compound CC1(C)CNNC1=O FJWJYHHBUMICTP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QMJDEXCUIQJLGO-UHFFFAOYSA-N [4-(methylamino)phenyl] hydrogen sulfate Chemical compound CNC1=CC=C(OS(O)(=O)=O)C=C1 QMJDEXCUIQJLGO-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 2
- 229960002449 glycine Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- ZZEYCGJAYIHIAZ-UHFFFAOYSA-N 4-methyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)CN1C1=CC=CC=C1 ZZEYCGJAYIHIAZ-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- FIARATPVIIDWJT-UHFFFAOYSA-N 5-methyl-1-phenylpyrazolidin-3-one Chemical compound CC1CC(=O)NN1C1=CC=CC=C1 FIARATPVIIDWJT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- -1 amino, substituted amino Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 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
- 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
- G03C5/3028—Heterocyclic compounds
- G03C5/3035—Heterocyclic compounds containing a diazole ring
Definitions
- R1, R2 and R3 are the same or dififerent and are hydrogen atoms or hydrocarbon groups, for instance alkyl groups, e. g. methyl, ethyl, propyl, isopropyl, or higher alkyl groups, aryl groups, e. g. phenyl or naphthyl groups, or aralkyl groups, e. g. benzyl groups.
- hydrocarbon substituent groups may themselves be substituted; for example, aryl groups may contain hydroxy, alkoxy, aryloxy, oxyalkyl, amino, substituted amino, sulphonic, carboxylic or halogen substituents.
- the said specification proposes, inter alia, the formulation of developers containing hydroquinone or pyrogallic acid, which are themselves effective developing agents, in addition to the 3-pyrazolidone.
- a developing composition comprises, in alkaline solution (and preferably weakly alkaline solution), p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone.
- alkaline solution and preferably weakly alkaline solution
- p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone.
- 3-pyrazolidones While the broad class of 3-pyrazolidones referred to above are generally useful, the preferred 3-pyrazolidones are the l-aryl-B-pyrazolidones, and particularly the l-phenyl-3-pyrazolidones, which are unsubstituted or substituted only by alkyl groups in the 4- and -positions. Specific 3-pyrazolidones of value are:
- EXAMPLE 1 Developer composition G. p-Hydroxyphenyl amino acetic acid -c 5 l-phenyl-B-pyrazolidone 0.2 Sodium sulphite (anhydrous) 9O Borax l 2 Sodium carbonate (anhydrous) 2 Water to make 1 litre.
- Example 2 The developer composition of Example 1 was modified by using, instead of 1-phenyl-3-pyrazolidlone, 0.2 g. of l-phenyl4-methyl-3-pyrazolidone or 0.3 g. of l-phenyl- 4.4-dimethyl-3-pyrazolidone, and each gave very similar results.
- EXAMPLE 3 Concentrated developer Potassium sulphite solution 71% w./v ml 422 p-Hydroxyphenyl amino acetic acid g 40 l-phenyl-3-pyrazolidone g 2 Water to make 1 litre.
- solid caustic soda in quantity sufficient (usually about 13 g.) to bring the solution, after dilution with 9 parts of water, to a pH of 9.1.
- this developer is diluted with 9 volumes of water and applied to exposed photographic fast panchromatic film for 10 minutes at 68 F. A fine grain image of gamma about 0.6 is obtained. The developer has a high photographic speed. If the l-phenyl-3-pyrazolidone is omitted a negligible image is obtained even after 30 minutes at 68 F.
- the foregoing developer when diluted as indicated, can be kept in full stoppered bottles for three or more months without any substantial loss of developing activity.
- EXAMPLE 4 Potassium sulphite solution 74.3% w./v ml 400 p-I-Iydroxyphenyl amino acetic acid g 50 1-phenyl-3-pyrazolidone g 1.75 Potassium bromide g 8 Water to make 1 litre.
- a photographic developing composition which comprises an alkaline solution containing p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone.
- a photographic developing composition which comprises an alkaline solution containing p-hydroxyphenyl amino acetic acid and 1-pheny1-3-pyrazolidone.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid and 1-phenyl-3-pyrazo1idone.
- a photographic developing composition which comprises an alkaline solution containing p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone, said solution further containing an alkali metal carbonate.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid and 1-pheny1-3-pyrazolidone, said solution further containing an alkali metal carbonate.
- a photographic developing composition which comprises an alkaline solution containing p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone, said solution further containing an alkali sulphite.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid and 1-phenyl-3-pyrazolidone, said solution further containing an alkali sulphite.
- a photographic developing composition which comprises an alkaline solution containing p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone, said solution containing alkali metabisulphite.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid and 1-pheny1-3-pyrazolidone, said solution containing alkali metabisulphite.
- a photographic developing composition which comprises an alkaline solution containing p-hydroxyphenyl amino acetic acid and a 3-pyrazolidone, said solution containing an alkali metal bromide.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid and l-phenyl-B-pyrazolidone, said solution containing an alkali metal bromide.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid, 1phenyl-3-pyrazolidone, alkali sulphite and alkali carbonate.
- a photographic developing composition which comprises an alkaline solution at pH 9 to 10 containing p-hydroxyphenyl amino acetic acid, lphenyl-3-pyrazolidone, alkali sulphite, alkali hydroxide and potassium bromide.
- a photographic developing composition which comprises the following ingredients substantially in the quantities stated:
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24607/54A GB761301A (en) | 1954-08-24 | 1954-08-24 | Improvements in or relating to photographic developing compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2753265A true US2753265A (en) | 1956-07-03 |
Family
ID=10214320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US528547A Expired - Lifetime US2753265A (en) | 1954-08-24 | 1955-08-15 | Photographic developing compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2753265A (fr) |
| BE (1) | BE540750A (fr) |
| CH (1) | CH337073A (fr) |
| DE (1) | DE1007621B (fr) |
| FR (1) | FR1139300A (fr) |
| GB (1) | GB761301A (fr) |
| NL (2) | NL199904A (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284200A (en) * | 1962-06-07 | 1966-11-08 | Ilford Ltd | 3-pyrazolidone developers |
| US5210010A (en) * | 1991-05-15 | 1993-05-11 | Ilford Limited | Silver halide developing solutions |
| US5998110A (en) * | 1996-12-11 | 1999-12-07 | Ferrania S.P.A. | Photographic silver halide developer composition and process for forming photographic silver images |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3778267A (en) * | 1971-10-14 | 1973-12-11 | Us Air Force | Photographic developer |
| JPS58160948A (ja) * | 1982-03-18 | 1983-09-24 | Konishiroku Photo Ind Co Ltd | リツプマン型ハロゲン化銀写真感光材料 |
| FR2743905B1 (fr) * | 1996-01-23 | 1999-03-05 | Kodak Pathe | Composition de revelateur organique-inorganique |
-
0
- NL NL88950D patent/NL88950C/xx active
- NL NL199904D patent/NL199904A/xx unknown
- BE BE540750D patent/BE540750A/xx unknown
-
1954
- 1954-08-24 GB GB24607/54A patent/GB761301A/en not_active Expired
-
1955
- 1955-08-15 US US528547A patent/US2753265A/en not_active Expired - Lifetime
- 1955-08-20 DE DEI10573A patent/DE1007621B/de active Pending
- 1955-08-23 CH CH337073D patent/CH337073A/de unknown
- 1955-08-23 FR FR1139300D patent/FR1139300A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284200A (en) * | 1962-06-07 | 1966-11-08 | Ilford Ltd | 3-pyrazolidone developers |
| US5210010A (en) * | 1991-05-15 | 1993-05-11 | Ilford Limited | Silver halide developing solutions |
| US5998110A (en) * | 1996-12-11 | 1999-12-07 | Ferrania S.P.A. | Photographic silver halide developer composition and process for forming photographic silver images |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1139300A (fr) | 1957-06-27 |
| CH337073A (de) | 1959-03-15 |
| NL199904A (fr) | |
| NL88950C (fr) | |
| GB761301A (en) | 1956-11-14 |
| BE540750A (fr) | |
| DE1007621B (de) | 1957-05-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2289367A (en) | Photographic developer | |
| US2691589A (en) | Photographic developer compositions | |
| GB767700A (en) | Improvements in photographic developer compositions | |
| US4310622A (en) | Photographic development process | |
| US3247201A (en) | 1-carbocyclic aryl-2-tertiary amino-3, 4-hydrocarbon and carbocyclic aryl-3-pyrazolidones | |
| US3867151A (en) | General purpose monobath | |
| US2753265A (en) | Photographic developing compositions | |
| US3232761A (en) | Hardening of photographic gelatin layers | |
| US2902367A (en) | Photographic developer antioxidant | |
| CA1135555A (fr) | Revelateur couleurs contenant un derive diamine d'un phenylene et un antioxydant du type aminocarbonyle | |
| US2271229A (en) | Fog inhibitor for photographic developers | |
| GB1251558A (fr) | ||
| US2685516A (en) | Photographic developer composition | |
| US2384593A (en) | Antifoggant | |
| US2311428A (en) | Photographic developer | |
| US2477323A (en) | Photographic developers | |
| US3713826A (en) | Sulfite esters as preservatives for black and white developing agents | |
| GB803783A (en) | Photographic materials | |
| GB767703A (en) | Improvements in direct positive photographic processes | |
| EP0446457B1 (fr) | Révélateur photographique alcalin pour noir et blanc | |
| GB767701A (en) | Improvements in photographic developer compositions | |
| US3380829A (en) | Photographic developing compositions | |
| US2852374A (en) | Photographic developer | |
| US2979406A (en) | Single powder photographic developers | |
| GB873198A (en) | Improvements in photographic developers and in reversal processes of colour photography |