US3833377A - Process for preparing granular color developing agent - Google Patents
Process for preparing granular color developing agent Download PDFInfo
- Publication number
- US3833377A US3833377A US00281672A US28167272A US3833377A US 3833377 A US3833377 A US 3833377A US 00281672 A US00281672 A US 00281672A US 28167272 A US28167272 A US 28167272A US 3833377 A US3833377 A US 3833377A
- Authority
- US
- United States
- Prior art keywords
- developing agent
- color developing
- mixture
- granular
- preparing
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 235000019441 ethanol Nutrition 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 229920013820 alkyl cellulose Polymers 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 21
- 238000004898 kneading Methods 0.000 abstract description 13
- 150000001298 alcohols Chemical class 0.000 abstract description 6
- 238000005469 granulation Methods 0.000 description 20
- 230000003179 granulation Effects 0.000 description 20
- 239000000843 powder Substances 0.000 description 14
- 238000001125 extrusion Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- TXBQVOWAZRPPHI-UHFFFAOYSA-N 4-N-ethylbenzene-1,4-diamine sulfuric acid Chemical compound S(=O)(=O)(O)O.NC1=CC=C(NCC)C=C1 TXBQVOWAZRPPHI-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- GVEYRUKUJCHJSR-UHFFFAOYSA-N (4-azaniumyl-3-methylphenyl)-ethyl-(2-hydroxyethyl)azanium;sulfate Chemical compound OS(O)(=O)=O.OCCN(CC)C1=CC=C(N)C(C)=C1 GVEYRUKUJCHJSR-UHFFFAOYSA-N 0.000 description 2
- OFXNTSSMLZYOEU-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine;sulfuric acid;hydrate Chemical compound O.OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 OFXNTSSMLZYOEU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- REMLBIQDWYHALC-UHFFFAOYSA-N n-[2-(4-amino-n-ethylanilino)ethyl]methanesulfonamide;sulfuric acid Chemical compound OS(O)(=O)=O.CS(=O)(=O)NCCN(CC)C1=CC=C(N)C=C1 REMLBIQDWYHALC-UHFFFAOYSA-N 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- KAJALVWKFPQZOO-UHFFFAOYSA-N (4-azaniumylphenyl)-ethyl-(2-hydroxyethyl)azanium;sulfate Chemical compound OS(O)(=O)=O.OCCN(CC)C1=CC=C(N)C=C1 KAJALVWKFPQZOO-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- -1 beta-hydroxyethyl Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning 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
- 150000003839 salts Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003232 water-soluble binding agent 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
- G03C5/264—Supplying of photographic processing chemicals; Preparation or packaging thereof
- G03C5/265—Supplying of photographic processing chemicals; Preparation or packaging thereof of powders, granulates, tablets
Definitions
- p-Phenylenediamine color developing agents are known in the art, and may be used either in their free form or in their salt form. For example, some of the compounds are described in US. Pat. No. 2,193,015 (1940) and 2,108,243 (1938); British Pat. No. 778,437 (1957); J. Am. Chem. Soc, Vol. 73, pp 3100 3125 1951), etc.
- p-phenylenediamine color developing agents (hereinafter referred to as merely color developing agent) have heretofore been marketed as fine powders. However, they are so light that they tend to scatter and, in addition, they will cause medicinal dermatitis (poisoning) on the parts of a body contacting them due to their toxicity (mainly dermatitis problems). In addition, some of these color developing agents become difficult to handle due to the solidification during storage even though, when they were produced, they were powders tending to scatter.
- the proportion of excipients can be varied depend ing upon the kind of color developing agent and the conditions of the powder thereof, but, in general, from 0.2 to 1.3 Kg of excipients per 10 Kg of the color developing agent are preferably used.
- Suitable excipients such as water or lower alcohols having a boiling point of lower than C, such as methyl alcohol, ethyl alcohol, isopropyl alcohol, etc. are preferably employed. Higher alcohols are not preferred because they require a long drying time due to their high boiling point during which the qualities of the color developing agents tend to be degraded, and because of their bad smell or poor working properties due to the solidifying characteristic of some of them.
- the addition of the excipient is preferably conducted incrementally since a large addition of excipient makes the kneaded product paste-like, which requires a long time in drying.
- an alkyl cellulose such as methyl cellulose, ethyl cellulose or propyl cellulose per 10 Kg of the color developing agent is added together with the excipient and, after kneading sufficiently, the kneaded mixture is extruded in the form of a rod, and then dried at an appropriate temperature.
- the proportion of the excipients can be determined by previously measuring the reduction in weight on drying (the reduction in weight should be preferably less than 10 percent and, if above 10 percent, drying or processing should be conducted), and subtracting the reduction in weight. Then kneading and granulating are conducted in the same manner as with dried powders, and subsequently, drying is conducted.
- the mixing and kneading work are preferably conducted using a kneader, and the extrusion is conveniently conducted using a screw extruder, etc.
- a fluidized layer drier is used for drying.
- the granular product of the color developing agent thus granulated and dried shows increased solubility in water due to the porous structure provided thereto, and, in a dry condition, the shape thereof by the usual vibration and shock in wrapping, transport, etc., is not easily lost and no powdery dust is produced.
- the problems previously encountered with medicinal dermatitis never occur.
- the smaller surface area in comparison with the finely powdered products serves to prevent air-oxidation, and
- the granular product can be weighed out with a measuring spoon or a measuring cup, which markedly shortens the wrapping and processing time and serves to improve the working property.
- Crushing weight One particle of a color developing agent formulated into granules is removed, and a load is applied thereto to measure the weight on crushing.
- Solidifying property with the lapse of time 100 grams of a granulated product is left in a closed glass bottle for 3 months.
- Oxidizability A granulated product and a powdered product were left in an atmosphere for 2 months, and the degree of discoloration was observed for a comparison of oxidizability.
- Solubility 1 gram of each of a powdery product and a granulated product was weighed out and the time required to dissolve it in ml of water at room temperature was measured for comparison.
- EXAMPLE 1 temperature.
- the resulting cake thus kneaded was subjected to a screw extrusion to mold it into a rod of 1.0 1.5 mm in diameter.
- the resulting rod was dried using a hot air fluidized bed drier at a temperature below 80 C, and the granules formed which passed through a 1680a sieve and did not pass through a 250;; sieve were collected to obtain 9.9 Kg of the granules.
- the resulting granulated product had a crushing weight of 150 g and was not crushed by usual vibrations and shock. Therefore, no dust was formed.
- EXAMPLE 2 400 ml of a mixed solution of water and ethyl alcohol of a concentration of 50 percent was sprayed over 10 Kg of the wet powder of the color developing agentprepared according to the process described in Example 1 and containing a mixture of water and ethyl alcohol whose reduction in weight on drying was 4 percent, while kneading in a kneader. After kneading for 15 minutes, the mixture was subjected to screw extrusion to mold it into a rod of 1.0 1.5 mm in diameter, and 9.5 Kg of the granulated product was obtained in the same manner as described in Example 1. Crushing weight: 140 g; Solubility: seconds (before granulation), 60 seconds (after granulation); Solidifying property: the granulated product did not solidify after 3 months; Oxidizability: the granulated product did not discolor.
- EXAMPLE 3 50 grams of methyl cellulose was added to a dried material of the color developing agent prepared according to the process described in Example 1 while kneading in a kneader, and 300 g of water was sprayed over the mixture. After kneading the mixture for 15 minutes at room temperature, the mixture was subjected to screw extrusion to mold it into a rod of 0.5 1.0 mm in diameter, and 9.5 Kg of the granulated product was obtained in the same manner as described in Example 1. Crushing weight: 230 g. Addition of methyl cellulose increased the crushing weight by a factor of about 2. Solubility in water: 40 seconds; Solidifying property: the granulated product did not solidify after 3 months. Oxidizability: the granulated product did not discolor.
- EXAMPLE 4 500 grams of isopropyl alcohol was sprayed over 10 Kg of the wet powder of the color developing agent having a reduction in weight on drying of 4 percent prepared according to the process described in Example 1 while kneading in a kneader. After kneading the mixture for 15 minutes at room temperature, the mixture was subjected to screw extrusion to mold it into a rod of 1.0 mm in diameter. Then, 9.3 Kg of the granulated product was obtained in the same manner as described in Example 1.
- Crushing weight 120 g
- Solubility 120 seconds (before granulation), 60seconds (after granulation); Solidifying property with the lapse of time: the granulated product did not solidify after 3 months; Oxidizability: the granulated product did not discolor.
- EXAMPLE 5 900 ml of a mixed solution of water and isopropyl alcohol of a concentration of 50 percent was sprayed over 10 Kg of the dried powdery material of 4-amino- N,N-diethylaniline monosulfate monohydrate, NH C H N(C H 'H SO 'H O, prepared according to the process described in British Pat. No. 778,437 (1957) while kneading in a kneader, and the mixture was kneaded for 15 minutes at room temperature. The 5 resulting cake was subjected to extrusion to mold it into a rod and granulated in the same manner as described in Example 1 to obtain 9.8 Kg of the granulated product.
- EXAMPLE 10 10 Kg of the dried powdery product of 4-amino-N- ethyl-N-(beta-methylsulfonamidoethyl)aniline mono- Sulfate, NH2C6H4N(C2H5)(CH2)ZNHSOZCH3'H2SO4,
- a process for preparing a granular color developing agent which comprises:
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/459,446 US3981732A (en) | 1971-08-19 | 1974-04-09 | Granular p-phenylenediamine color developing agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46063231A JPS511425B2 (enrdf_load_stackoverflow) | 1971-08-19 | 1971-08-19 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/459,446 Division US3981732A (en) | 1971-08-19 | 1974-04-09 | Granular p-phenylenediamine color developing agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3833377A true US3833377A (en) | 1974-09-03 |
Family
ID=13223218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00281672A Expired - Lifetime US3833377A (en) | 1971-08-19 | 1972-08-18 | Process for preparing granular color developing agent |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3833377A (enrdf_load_stackoverflow) |
| JP (1) | JPS511425B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2240777A1 (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3981732A (en) * | 1971-08-19 | 1976-09-21 | Fuji Photo Film Co., Ltd. | Granular p-phenylenediamine color developing agent |
| US5258268A (en) * | 1990-08-11 | 1993-11-02 | Agfa Gevaert Aktiengesellschaft | Photochemicals with reduced dust formation |
| EP0711592A3 (en) * | 1994-11-11 | 1997-03-05 | Konishiroku Photo Ind | Solid composition manufacturing method for processing photosensitive silver halide photographic materials |
| US5635342A (en) * | 1994-04-19 | 1997-06-03 | Konica Corporation | Method for manufacturing solid processing composition for silver halide photographic light-sensitive materials |
| US5780211A (en) * | 1991-05-01 | 1998-07-14 | Konica Corporation | Processing composition in the tablet form for silver halide photographic light-sensitive material |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1579481A (en) * | 1977-02-18 | 1980-11-19 | Ciba Geigy Ag | Preparation of photographic material |
| US4816384A (en) * | 1986-10-09 | 1989-03-28 | E. I. Du Pont De Nemours And Company | Powdered packaged developer |
| JPH0485534A (ja) * | 1990-07-30 | 1992-03-18 | Konica Corp | 写真用処理剤の固形化方法 |
| JPH0485533A (ja) * | 1990-07-30 | 1992-03-18 | Konica Corp | 写真用処理剤の固形化方法 |
| JPH04172341A (ja) * | 1990-11-05 | 1992-06-19 | Konica Corp | 写真用処理剤の固形化方法及び写真用処理剤 |
| EP4368839A4 (en) | 2022-01-21 | 2025-07-09 | Hitachi Construction Mach Co | WORKING MACHINE |
| EP4375516A4 (en) | 2022-01-25 | 2025-07-30 | Hitachi Construction Mach Co | Work machine |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1343833A (en) * | 1918-11-14 | 1920-06-15 | Leitch John Walker | Apparatus for solidifying or concentrating materials |
| US2850764A (en) * | 1953-09-01 | 1958-09-09 | Ici Ltd | Process and apparatus for converting thermoplastic material to granular form |
| US3114930A (en) * | 1961-03-17 | 1963-12-24 | American Cyanamid Co | Apparatus for densifying and granulating powdered materials |
| GB962843A (en) * | 1961-06-02 | 1964-07-08 | Emil Hutt | Improvements in or relating to methods of and apparatus for producing granulates andthe like from powder substances |
| US3297760A (en) * | 1959-07-23 | 1967-01-10 | Fairmount Chem | Para amino-nu-ethyl-nu-beta-hydroxy-ethyl-meta toluidine mono-nitrate and di-nitrate nd methods of producing same |
| DE1936247A1 (de) * | 1968-07-19 | 1970-01-22 | Ici Ltd | Verfahren zur Herstellung von tablettenfoermigen wasserloeslichen Substanzen |
-
1971
- 1971-08-19 JP JP46063231A patent/JPS511425B2/ja not_active Expired
-
1972
- 1972-08-18 DE DE2240777A patent/DE2240777A1/de active Pending
- 1972-08-18 US US00281672A patent/US3833377A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1343833A (en) * | 1918-11-14 | 1920-06-15 | Leitch John Walker | Apparatus for solidifying or concentrating materials |
| US2850764A (en) * | 1953-09-01 | 1958-09-09 | Ici Ltd | Process and apparatus for converting thermoplastic material to granular form |
| US3297760A (en) * | 1959-07-23 | 1967-01-10 | Fairmount Chem | Para amino-nu-ethyl-nu-beta-hydroxy-ethyl-meta toluidine mono-nitrate and di-nitrate nd methods of producing same |
| US3114930A (en) * | 1961-03-17 | 1963-12-24 | American Cyanamid Co | Apparatus for densifying and granulating powdered materials |
| GB962843A (en) * | 1961-06-02 | 1964-07-08 | Emil Hutt | Improvements in or relating to methods of and apparatus for producing granulates andthe like from powder substances |
| DE1936247A1 (de) * | 1968-07-19 | 1970-01-22 | Ici Ltd | Verfahren zur Herstellung von tablettenfoermigen wasserloeslichen Substanzen |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3981732A (en) * | 1971-08-19 | 1976-09-21 | Fuji Photo Film Co., Ltd. | Granular p-phenylenediamine color developing agent |
| US5258268A (en) * | 1990-08-11 | 1993-11-02 | Agfa Gevaert Aktiengesellschaft | Photochemicals with reduced dust formation |
| US5780211A (en) * | 1991-05-01 | 1998-07-14 | Konica Corporation | Processing composition in the tablet form for silver halide photographic light-sensitive material |
| US5635342A (en) * | 1994-04-19 | 1997-06-03 | Konica Corporation | Method for manufacturing solid processing composition for silver halide photographic light-sensitive materials |
| EP0711592A3 (en) * | 1994-11-11 | 1997-03-05 | Konishiroku Photo Ind | Solid composition manufacturing method for processing photosensitive silver halide photographic materials |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2240777A1 (de) | 1973-03-01 |
| JPS4829433A (enrdf_load_stackoverflow) | 1973-04-19 |
| JPS511425B2 (enrdf_load_stackoverflow) | 1976-01-17 |
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