GB765286A - Photographic developers - Google Patents

Photographic developers

Info

Publication number
GB765286A
GB765286A GB7555/55A GB755555A GB765286A GB 765286 A GB765286 A GB 765286A GB 7555/55 A GB7555/55 A GB 7555/55A GB 755555 A GB755555 A GB 755555A GB 765286 A GB765286 A GB 765286A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
carboxylic acid
prepared
amino
phenyl
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
Application number
GB7555/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agfa Gevaert NV
Original Assignee
Agfa AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Agfa AG filed Critical Agfa AG
Publication of GB765286A publication Critical patent/GB765286A/en
Expired legal-status Critical Current

Links

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

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)

Abstract

765,286. 4-Amino-5-pyrazolone derivatives. AGFA AKT. - GES. FUR PHOTOFABRIKATION. March 15, 1955 [March 15, 1954], No. 7555/55. Class 2 (3). [Also in Group XX] 1 - Phenyl- 4 - amino - 5 - pyrazolone - 3 - carboxylic acid amide is prepared by heating together in an autoclave 1-phenyl-5-pyrazolone- 3-carboxylic acid ethyl ester and ammonia, dissolving the product in water, adding sodium nitrite, and introducing the solution into hydrochloric acid, and reducing the isonitroso compound so obtained with zinc dust and acetic acid. 1 - Phenyl - 4 - amino - 5 - pyrazolone- 3-carboxylic acid ethanolamine is similarly prepared. 1 - Phenyl - 4 - amino - 5 - pyrazolone - 3 - - carboxylic acid methanesulphohydrazide is prepared by adding methanesulphochloride and sodium hydroxide simultaneously to a sodium hydroxide solution of 1-phenyl-5-pyrazolone-3-carboxylic acid hydrazide (prepared by refluxing together 1 - phenyl - 5 - pyrazolone - 3 - carboxylic acid ethyl ester and hydrazine hydrate in ethanol), reacting the product with sodium nitrite and hydrochloric acid to obtain the isonitroso compound, and reducing this with tin sponge and hydrochloric acid. 4 - Amino - 5 - pyrazolone - 3 - carboxylic acid ethyl ester is prepared by heating together sodium acetate, the sodium salt of ethyl oxalacetate and hydrazine sulphate in water, forming the isonitroso derivative by reaction with sodium nitrite and hydrochloric acid, and reducing with tin sponge and hydrochloric acid. 1 - Phenyl - 4 - amino - 5 - pyrazolone - 3 - carboxylic acid hydrazide is prepared by converting 1 - phenyl - 5 - pyrazolone - 3 - carboxylic acid ethyl ester to the isonitroso derivative, reacting with hydrazine hydrate, and reducing with tin sponge and hydrochloric acid. 1 - - p - Sulphophenyl - 4 - amino - 5 - pyrazolone- 3-carboxylic acid ethyl ester is prepared by converting 1 - p - - sulphophenyl - 5 - pyrazolone- 3-carboxylic acid ethyl ester to the isonitroso derivative and reducing with tin sponge and hydrochloric acid. 1-p-Ethoxyphenyl-4-amino- 5-pyrazolone-3-carboxylic acid is similarly prepared. 1 - p - Aminophenyl - 4 - amino - 5 - pyrazo- Zone-3-carboxylic acid ethyl ester is prepared by converting 1 - p - nitrophenyl - 5 - pyrazolone- 3-carboxylic acid ethyl ester to the isonitroso derivative and reducing with tin sponge and hydrochloric acid. 1 - p - Ethoxyphenyl - 5 - pyrazolone - 3 - carboxylic acid is prepared by reacting together p - ethoxyphenylhydrazine hydrochloride, ethanol, sodium acetate, and the sodium salt of ethyl oxalacetate. 1 - (2 - Tetrahydrothiophenesulphone) - 4- amino - 5 - pyrazolone - 3 - carboxylic acid ethyl ester is prepared by reacting together hydrazine and butadiene sulphone, heating the product with sodium oxalate, ethanol, and glacial acetic acid, and forming the isonitroso derivative and reducing with tin sponge and hydrochloric acid. 1 - Phenyl - 4 - amino - 5 - pyrazolone - 3 - carboxylic acid is prepared by reacting 1-phenyl-5- pyrazolone-3-carboxylic acid with benzenediazonium chloride and reducing the azo dye formed with tin sponge and hydrochloric acid. Specification 459,665, [Group IV], is referred to.
GB7555/55A 1954-03-15 1955-03-15 Photographic developers Expired GB765286A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA19873A DE955025C (en) 1954-03-15 1954-03-15 Photographic developer

Publications (1)

Publication Number Publication Date
GB765286A true GB765286A (en) 1957-01-09

Family

ID=43015123

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7555/55A Expired GB765286A (en) 1954-03-15 1955-03-15 Photographic developers

Country Status (6)

Country Link
US (1) US2981623A (en)
BE (1) BE536351A (en)
CH (1) CH335940A (en)
DE (1) DE955025C (en)
FR (1) FR1124976A (en)
GB (1) GB765286A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3012884A (en) * 1956-12-31 1961-12-12 Gevaert Photo Prod Nv Production of colored photographic images

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1029229B (en) * 1956-12-22 1958-04-30 Agfa Ag Photographic developer
US3386825A (en) * 1957-07-02 1968-06-04 Polaroid Corp Photographic product containing zinc
BE578539A (en) * 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
US3285150A (en) * 1961-05-16 1966-11-15 Wunder Phot Inc Combined photographic and development apparatus
NL286908A (en) * 1961-12-19
BE637358A (en) * 1962-09-15
JPH0648371B2 (en) * 1986-11-07 1994-06-22 富士写真フイルム株式会社 Processing method of silver halide photographic light-sensitive material for X-ray

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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
DE685901C (en) * 1935-08-31 1939-12-28 I G Farbenindustrie Akt Ges Process for fine grain development

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3012884A (en) * 1956-12-31 1961-12-12 Gevaert Photo Prod Nv Production of colored photographic images

Also Published As

Publication number Publication date
CH335940A (en) 1959-01-31
US2981623A (en) 1961-04-25
DE955025C (en) 1956-12-27
FR1124976A (en) 1956-10-22
BE536351A (en) 1955-09-09

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