US2981623A - Photographic developers - Google Patents
Photographic developers Download PDFInfo
- Publication number
- US2981623A US2981623A US494221A US49422155A US2981623A US 2981623 A US2981623 A US 2981623A US 494221 A US494221 A US 494221A US 49422155 A US49422155 A US 49422155A US 2981623 A US2981623 A US 2981623A
- Authority
- US
- United States
- Prior art keywords
- pyrazolone
- amino
- carboxylic acid
- filtered
- developer
- 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 claims description 20
- -1 SILVER HALIDE Chemical class 0.000 claims description 14
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000126 substance Substances 0.000 description 21
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 13
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- GWXFTBJDOGGQIC-UHFFFAOYSA-N 4-amino-5-phenylpyrazol-3-one Chemical compound N1=NC(=O)C(N)=C1C1=CC=CC=C1 GWXFTBJDOGGQIC-UHFFFAOYSA-N 0.000 description 3
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 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 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ACOIYJJFAXRSHM-UHFFFAOYSA-N 5-aminopyrazol-3-one Chemical compound NC1=CC(=O)N=N1 ACOIYJJFAXRSHM-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RROBGBQPYPYDFT-UHFFFAOYSA-N (4-ethoxyphenyl)hydrazine;hydrochloride Chemical compound Cl.CCOC1=CC=C(NN)C=C1 RROBGBQPYPYDFT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- XXZCIYUJYUESMD-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(morpholin-4-ylmethyl)pyrazol-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)CN1CCOCC1 XXZCIYUJYUESMD-UHFFFAOYSA-N 0.000 description 1
- MEJAPGGFIJZHEJ-UHFFFAOYSA-N 5-acetamido-1,3,4-thiadiazole-2-sulfonyl chloride Chemical compound CC(=O)NC1=NN=C(S(Cl)(=O)=O)S1 MEJAPGGFIJZHEJ-UHFFFAOYSA-N 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/24—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms having sulfone or sulfonic acid radicals in the molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/50—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- the present invention relates to photographic developer substances and more especially to substances derived from 4-amino-pyrazolones-(S -As photographic developers, it has been the practice hitherto generally to employ substances which belong to the class of aromatic polyvalent hyd'roxy compounds, amino-hydroxy compounds or polyvalent amino compounds.
- Compounds of the heterocyclic class are known to have developer properties (German Patent No. 646,516), inter alia, S-pyrazolones, substituted in the 4-position with an amino group, which S-pyrazolorles contain the m-aminoketone structurein the heterocyclic nucleus.
- These aminopyrazolones are, however, exclusively substances which are alkylated in the 3-position.
- These compounds have not been used in practice as developers, since they are quite unstable with relatively small intensity of development and show a strong tendency to fogging.
- R may represent -OH, O-alkyl, O-aryl, O-aralkyl NH or substituted NH groups, NHNH or substituted hydrazide groups, NHOH or an azide group and also alkyl, aryl or aralkyl radicals.
- R may represent hydrogen, alkyl, aralkyl, aryl groups or substituted aryl groups or heterocyclic radicals.
- Such compounds represent excellent photographic developer substances, since they operate without fogging with a surprisingly high development intensity and are sufficiently stable in order to be used practically as developers.
- the developer substances may either be used independently or with advantage in combination with known developer substances, whereby they either work more quickly owing to their great rapidity, i.e. develop images to the same gamma value in a shorter time, or they develop a specific photographic material to higher gamma values with the same development period.
- the property of the present invention may be incorporated into silver super-additivity may also frequently be used with adhalide emulsion layers which are developed by alkaline solution containing, if desired, developer substances.
- aminopyrazolones are produced according to known processes.
- suitable pyrazolones may be transformed by treatment with nitrite into the isonitroso-compounds and the latter by reduction with tin into the associated amino compounds.
- the reduction of the isonitroso-cornpounds may also be carried out according to other known processes, for example with zinc and glacial acetic acid or catalytically.
- Another available method for the production of such compounds is based upon the reductive splitting of azo dyestuifs, which are obtained. by coupling suitable pyrazolones with diazonium salts.
- the isonitroso compound can be reduced with tin sponge and hydrochloric acid according to the process described in Arch. Pharm., 278 (1940), p. 330.
- 430 g. of the pyrazolone are dissolved in 1000 cc. of hydrochloric acid 1:1) at 50 C., the undissolved portion is separated by filtering and the solution is mixed at lO-15 C. with 170 g. of nitrite in 300 cc. of water. After filtering with suction, washing water and drying 380 g. of isonitroso derivative are obtained.
- the deriva tive is mixed with 100 cc. of alcohol, reacted while stirring with 1000 cc. of hydrochloric acid and reduced by gradual addition of 250 g. of tin sponge within 5 hours.
- the hydrochloride is filtered with suction, dissolved in 1000 Iclc. of hot water, filtered and precipitated in the cold wit cc. of hydrochloric acid. After filtering with suction, washing with little water and drying in vacuum.
- 1-phenyl-4-amino-5-pyrazolone-3-carboxylic acid hydrazide can be prepared as follows:
- reaction product is reduced with tin sponge and hydrochloric acid according to Arch. Pharm, 278 (1940), p. 330.
- This aminopyrazolone is produced according to Arch. Pharm, 278 (1940), p. 330.
- EXAMPLE 7 In the developer of Example 3, the hydrochloride of 4-amino-5-pyrazolone-3-carboxylic acid ester is replaced by 15 g. of 1-(p-sulfophenyl)-4-amino-5-pyrazolone-3- carboxylic acid ethyl ester.
- the developer is of high stability and develops negatives brilliantly and free from fogging.
- 34 g'. of the nitroso compound are mixed with stirring with 20 cc. ofalcohol and 120 cc. of hydrochloric acid and reduced with 24 g. of tin sponge as usual.
- the aminopyrazolone is filtered with suction and recrystallized from water.
- the ethanol amide is dissolved in sodium hydroxide solution (3%), mixed with 8 g. of nitrite, introduced with stirring into hydrochloric acid (10%), filtered with suction and recrystallized from alcohol.
- EXAMPLE 9 1 (p-aminophenyl)-4-amino-5-pyrazolone-3-carboxylic acid ethyl ester hydrochloride g 3 Sodium sulfite anhydrous g 40 Hydroquinone g 6 Soda g 20 Potassium bromide -g 1 Water cc Up to 1000 Soft-acting negative developer for orthochromatic and panchromatic photographic materials; development period: 5 minutes.
- EXAMPLE l1 1 (2'-tetrahydrothiophenesulfone)-4-amino-5-pyrazolone-3-carboxylic acid ethyl ester hydrochloride g 14 Sodium sulfite anhydrous g 125 Soda 6 Potassium bromide g 2.5 Water cc Up to 1000 Very soft fine-grain developer; development period: 12-14 minutes.
- EXAMPLE 12 1 phenyl 4 amino 5 pyrazolone 3 carboxylic acid g 1.6 Sodium sulfite anhydrous g 45 Hydroquinone g 1.2 Soda g 8 Potassium-meta bi-sulfite (K S O g 4 Potassium bromide g 1 Water cc Up to 1000 Normal negative developer; development periods: 10 12 minutes.
- the process of developing silver halide layers which comprises applying to said'layers a compound having a formula selected from the group consisting of and wherein R is a radical selected from the group consisting of OH, O-alkyl, O-aryl, O-aralkyl, NH NH-- NH and -NHOH, and R is selected from the group consisting of hydrogen, alkyl, aralkyl, aryl and Z-tetrahydrothiophene sulfone radicals, in an alkaline medium.
- R is a radical selected from the group consisting of OH, O-alkyl, O-aryl, O-aralkyl, NH NH-- NH and -NHOH
- R is selected from the group consisting of hydrogen, alkyl, aralkyl, aryl and Z-tetrahydrothiophene sulfone radicals, in an alkaline medium.
- a photographic developing composition consisting essentially of a compound having a formula selected from the group consisting of wherein R is a radical selected from the group consisting of OH, O-alkyl, O-aryl, O-aralkyl, NH NHNH and NH-OH, and R is selected from the group consisting of hydrogen, alkyl, aralkyl, aryl and 2-tetrahydroth-iophene sul-fone radicals, plus a compound selected from the group consisting of pyrocatechol, hydroquinone,
- a photographic developer comprising a silver halide developing compound having a formula selected from the class consisting of:
- a photographic developer according to claim 3 wherein said silver halide developing agent is l-phenyl- 4-amino-5-pyrazolone-3-carboxylic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA19873A DE955025C (de) | 1954-03-15 | 1954-03-15 | Photographischer Entwickler |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2981623A true US2981623A (en) | 1961-04-25 |
Family
ID=43015123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US494221A Expired - Lifetime US2981623A (en) | 1954-03-15 | 1955-03-14 | Photographic developers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2981623A (fr) |
| BE (1) | BE536351A (fr) |
| CH (1) | CH335940A (fr) |
| DE (1) | DE955025C (fr) |
| FR (1) | FR1124976A (fr) |
| GB (1) | GB765286A (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178441A (en) * | 1961-12-19 | 1965-04-13 | Ilford Ltd | Pyridyl-pyrazolidine 3-ones |
| US3285150A (en) * | 1961-05-16 | 1966-11-15 | Wunder Phot Inc | Combined photographic and development apparatus |
| US3295975A (en) * | 1962-09-15 | 1967-01-03 | Agfa Ag | Black-and-white developer for photographic reversal processes |
| US3386825A (en) * | 1957-07-02 | 1968-06-04 | Polaroid Corp | Photographic product containing zinc |
| US5187050A (en) * | 1986-11-07 | 1993-02-16 | Fuji Photo Film Co., Ltd. | Method for automatic processing of silver halide photographic material |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1029229B (de) * | 1956-12-22 | 1958-04-30 | Agfa Ag | Photographischer Entwickler |
| BE563474A (fr) * | 1956-12-31 | 1960-06-17 | ||
| BE578539A (fr) * | 1958-05-10 | |||
| US3034891A (en) * | 1958-07-31 | 1962-05-15 | Gen Aniline & Film Corp | Procedure for the production of yellow dye images by color development |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1937844A (en) * | 1931-03-23 | 1933-12-05 | Goodrich Co B F | Photographic developer and method of developing |
| US2139870A (en) * | 1935-08-31 | 1938-12-13 | Agfa Ansco Corp | Photographic developers |
| US2637732A (en) * | 1953-05-05 | Process for the manufacture of | ||
| US2731473A (en) * | 1956-01-17 | New pyrazolone derivatives |
-
1954
- 1954-03-15 DE DEA19873A patent/DE955025C/de not_active Expired
-
1955
- 1955-03-03 CH CH335940D patent/CH335940A/de unknown
- 1955-03-09 BE BE536351A patent/BE536351A/fr unknown
- 1955-03-14 US US494221A patent/US2981623A/en not_active Expired - Lifetime
- 1955-03-14 FR FR1124976D patent/FR1124976A/fr not_active Expired
- 1955-03-15 GB GB7555/55A patent/GB765286A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2637732A (en) * | 1953-05-05 | Process for the manufacture of | ||
| US2731473A (en) * | 1956-01-17 | New pyrazolone derivatives | ||
| US1937844A (en) * | 1931-03-23 | 1933-12-05 | Goodrich Co B F | Photographic developer and method of developing |
| US2139870A (en) * | 1935-08-31 | 1938-12-13 | Agfa Ansco Corp | Photographic developers |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3386825A (en) * | 1957-07-02 | 1968-06-04 | Polaroid Corp | Photographic product containing zinc |
| US3285150A (en) * | 1961-05-16 | 1966-11-15 | Wunder Phot Inc | Combined photographic and development apparatus |
| US3178441A (en) * | 1961-12-19 | 1965-04-13 | Ilford Ltd | Pyridyl-pyrazolidine 3-ones |
| US3295975A (en) * | 1962-09-15 | 1967-01-03 | Agfa Ag | Black-and-white developer for photographic reversal processes |
| US5187050A (en) * | 1986-11-07 | 1993-02-16 | Fuji Photo Film Co., Ltd. | Method for automatic processing of silver halide photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| BE536351A (fr) | 1955-09-09 |
| DE955025C (de) | 1956-12-27 |
| GB765286A (en) | 1957-01-09 |
| FR1124976A (fr) | 1956-10-22 |
| CH335940A (de) | 1959-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1581964A (en) | Method for forming images in silver halide photographic material | |
| US2981623A (en) | Photographic developers | |
| DE3127781C2 (fr) | ||
| GB1583471A (en) | Heterocyclic compounds and photographic materials containing them | |
| JPS6145239A (ja) | 内部潜像ハロゲン化銀写真乳剤 | |
| US3266897A (en) | Antifoggant agents for photography | |
| US2412700A (en) | Thioglycolic amides | |
| US2846307A (en) | Isoxazolone couplers in color photography | |
| US2465149A (en) | Tetrazolyl disulfides as stabilizing agents for silver-halide emulsions | |
| US4439519A (en) | Silver-halide photographic light-sensitive material | |
| US2271229A (en) | Fog inhibitor for photographic developers | |
| US3684514A (en) | Light-sensitive silver halide color photographic emulsions | |
| US2901351A (en) | Direct positive photographic material | |
| US2551134A (en) | Process of color developing with 2-thiohydantoin derivatives | |
| US4028320A (en) | Method of hardening gelatin using sulfonyl compounds | |
| US3010827A (en) | Photographic developer | |
| US3294542A (en) | Photosensitive diazo compositions | |
| US2710802A (en) | Dialkyl-5-(oxanilamido) isophthalate couplers for color photography | |
| US2695234A (en) | Photographic development | |
| US3762921A (en) | Photographic colour material | |
| US2448939A (en) | Thioglycolic amide couplers | |
| GB803783A (en) | Photographic materials | |
| US2632702A (en) | Pyrazolone couplers for color photography | |
| US2725291A (en) | Azo dye couplers having two coupling nuclei | |
| US2892714A (en) | Photographic color development with pyrazoline developers |