GB1239017A - - Google Patents

Info

Publication number
GB1239017A
GB1239017A GB865368A GB865368A GB1239017A GB 1239017 A GB1239017 A GB 1239017A GB 865368 A GB865368 A GB 865368A GB 865368 A GB865368 A GB 865368A GB 1239017 A GB1239017 A GB 1239017A
Authority
GB
United Kingdom
Prior art keywords
acid
prepared
bis
sulphobenzimidazole
pyridyl
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
GB865368A
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 filed Critical
Priority to GB865368A priority Critical patent/GB1239017A/en
Priority to FR6902993A priority patent/FR2002373A1/fr
Priority to DE19691906952 priority patent/DE1906952C2/en
Priority to JP1315169A priority patent/JPS4751896B1/ja
Priority to BE728728D priority patent/BE728728A/xx
Priority to US00141995A priority patent/US3808005A/en
Publication of GB1239017A publication Critical patent/GB1239017A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/28—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression

Abstract

1,239,017. Heterocyclic sulphonic acids. GEVAERT-AGFA N.V. 29 Jan., 1969 [22 Feb., 1968], No. 8653/68. Heading C2C. [Also in Division G2] 2 - (3 - Pyridyl) - 5(6) - sulphobenzimidazole, 2 - (4 - pyridyl) - 5(6) - sulphobenzimidazole monohydrate, 2 - (5 - sulpho - 2 - pyridyl) - 5(6)- sulphobenzimidazole dihydrate, N,N-bis (5(6)- sulpho - 2 - benzimidazolylmethyl)- methylamine, 2 - (5(6) - sulpho - 2 - benzamidazolyl) - 3H - imidazo [4,5 - b] pyridine, 2 - (4 - thiazolylmethyl)- 5(6) - sulphobenzimidazole and 3 - (m - sulphophenyl) - 5 - (2 - pyridyl) - pyrazole are prepared by treatment of the corresponding heterocyclic compound or mono-sulphonated derivative thereof with chlorosulphonic acid followed by hydrolysis of the sulphochloride formed. 1,4 - Bis (5(6) - sulpho - 2 - benzimidazolyl)- butane is obtained by sulphonation of the corresponding heterocyclic compound with fuming sulphuric acid. 1,2 - Bis (5 - tetrazolyl) - ethanesulphonic acid sodium salt is prepared by concentrating by evaporation a solution of 1,2-bis (5-tetrazolyl)- ethene in aqueous sodium hydrosulphite. 2 - (5 - Sulpho - 2 - pyridyl) benzimidazole is prepared by heating a mixture of 2-carboxy-5- sulphopyridine and o-phenylenediamine in polyphosphoric acid. 2 - (2 - Pyridyl) - 5(6) - sulphobenzimidazole . 1� hydrate, 2 - (4 - pyridyl) - 5(6)- sulphobenzimidazole . 2/3 phosphoric acid, 2,6-bis- (5(6) - sulpho - 2 - benzimidazolyl) pyridine monohydrate, 2 - [# - (2 - pyridyl) - vinyl] - 5(6) - sulphobenzimidazole hydrochloride monohydrate and 2 - (2 - quinolyl) - 5(6) - sulphobenzimidazole are prepared by heating a mixture of 3,4-diaminobenzosulphonic acid and picolinic acid, isonicotinic acid, 2,6-pyridinedicarboxylic acid, 2- (2-pyridyl) acrylic acid or 2-quinolinecarboxylic acid, respectively, in polyphosphoric acid. 1 - Ethyl - 2 - (2 - pyridyl) - 5 - sulphobenzimidazole and 2 - (2 - pyridyl) - 7 - sulpho - 1H- naphtho[1,2-d]imidazole are prepared by heating 3 - amino - 4 - ethylaminobenzenesulphonic acid and 1,2 - diaminonaphthalene - 6 - sulphonic acid respectively in picolinic acid dissolved in polyphosphoric acid. 1,2 - Bis - (5(6) - sulpho - 2 - benzimidazolyl)- ethane is prepared by refluxing a solution of 3,4- diaminobenzene-sulphonic acid and succinic acid in 6N hydrochloric acid. 1,3-Bis(5(6)- sulpho - 2 - benzimidazolyl) propane is prepared similarly but using glutaric acid instead of succinic acid. 2 - (2 - Pyrrolyl) - 5(6) - sulphobenzimidazole is prepared by refluxing a suspension of 3,4-diaminobenzene-sulphonic acid and 2-pyrrolecarbaldehyde sodium bisulphite addition product in ethanol. 1,2 - Bis - [5 - (3 - sulphopropylthio) - 1H - 1,2,4- triazol - 3 - yl] - ethane disodium salt is prepared by adding propanesultone to a solution of 1,2 - bis - (5 - mercapto - 1H - 1,2,4 - triazol - 3- yl) ethane (prepared as described in Bull. Soc. Chim. Belg. 75, 358 (1966)) and sodium methylate in methanol and refluxing. 1,2-Bis-[5-(1,3- dimethyl - 3 - sulphobutylthio) - 1H - 1,2,4 - triazol-3-yl] ethane disodium salt is prepared by adding 1,1,3 - trimethylpropane-sultone to a solution of 1,2-bis-(5-mercapto-1H-1,2,4-triazol- 3-yl(-ethane and sodium methylate in methanol and refluxing. 3 - (3 - Sulphopropylthio) - 5 - (4 - pyridyl)- 1H-1,2,4-triazole is prepared by adding propanesultone to a solution of 5-(4-pyridyl)-1H- 1,2,4 - triazole - 3 - thiol (prepared as described in Rec. Trav. Chim. Pays-Bas 73 (1954) 113) and sodium methylate in methanol and refluxing. 1,3 - Bis - [5 - (3 - sulphopropylthio) - 1H- 1,2,4 - triazol - 3 - yl] - propane is prepared similarly starting from 1,3-bis-(5-mercapto-lH- 1,2,4-triazol-3-yl)-propane. 2 - (2 - Benzimidazolylmethylthio)- 5(6) - sulphobenzimidazole is prepared by heating with stirring the disodium salt of 2-mercapto-5(6)- sulphobenzimidazole and 2-chloromethylbenzimidazole in dimethylformamide. 2-(2-Pyridylmethylthio) - 5(6) - sulphobenzimidazole is prepared similarly but using 2-chloromethylpyridine instead of the corresponding benzimidazole derivative. The disodium salt of 1,1-bis - [5(6)- sulpho - 2 - benzimidazolylthio] methane is prepared similarly from 2-mercapto-5(6)-sulphobenzimidazole and dibromomethane. 1,3 - Bis - [5 - sulpho - 1,2,4 - triazol - 3 - yl]- propane is prepared by adding dropwise an aqueous solution of potassium permanganate to an aqueous solution of 1,3-bis (5-mercapto-1H- 1,2,4-triazol-3-yl)-propane until the colour did not disappear any more.
GB865368A 1968-02-22 1968-02-22 Expired GB1239017A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB865368A GB1239017A (en) 1968-02-22 1968-02-22
FR6902993A FR2002373A1 (en) 1968-02-22 1969-02-07
DE19691906952 DE1906952C2 (en) 1968-02-22 1969-02-12 Photographic material
JP1315169A JPS4751896B1 (en) 1968-02-22 1969-02-20
BE728728D BE728728A (en) 1968-02-22 1969-02-21
US00141995A US3808005A (en) 1968-02-22 1971-05-10 Silver halide emulsion stabilized with a bidentate heterocyclic compound containing a sulpho or a carboxyl group

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB865368A GB1239017A (en) 1968-02-22 1968-02-22

Publications (1)

Publication Number Publication Date
GB1239017A true GB1239017A (en) 1971-07-14

Family

ID=9856631

Family Applications (1)

Application Number Title Priority Date Filing Date
GB865368A Expired GB1239017A (en) 1968-02-22 1968-02-22

Country Status (5)

Country Link
JP (1) JPS4751896B1 (en)
BE (1) BE728728A (en)
DE (1) DE1906952C2 (en)
FR (1) FR2002373A1 (en)
GB (1) GB1239017A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5409809A (en) * 1992-10-01 1995-04-25 E. I. Du Pont De Nemours And Company Silver halide emulsions stabilized with improved antifoggants

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3216843C2 (en) * 1982-05-05 1986-10-23 Ludwig Heumann & Co GmbH, 8500 Nürnberg 3-Thiomethyl-pyridine derivatives, processes for their preparation and pharmaceuticals containing these compounds
EP0218753B1 (en) * 1985-10-10 1989-08-09 Agfa-Gevaert N.V. Image-recieving element for the silver salt diffusion transfer reversal process
JPH0833642B2 (en) * 1986-10-24 1996-03-29 富士写真フイルム株式会社 Development processing method of silver halide photographic light-sensitive material
KR101540145B1 (en) * 2012-02-15 2015-07-28 삼성전기주식회사 Alkyl sulphonated tetrazole compound, preparing method thereof, and epoxy resin containing the same, and substrate produced therefrom
KR101747259B1 (en) * 2012-12-28 2017-06-14 삼성전기주식회사 Surface modified silica by alkyl sulphonated tetrazole compound, preparing method thereof, and resin composition containing the same
KR101956281B1 (en) * 2013-08-13 2019-03-08 삼성전기주식회사 Resin composition, printed circuit board using the composition, and preparing method thereof
KR101956273B1 (en) * 2013-08-13 2019-03-08 삼성전기주식회사 Resin composition, printed circuit board using the composition, and preparing method thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE498287A (en) * 1949-09-24
BE498286A (en) * 1949-09-24
DE1177481B (en) * 1963-05-18 1964-09-03 Agfa Ag Photographic light-sensitive material having at least one sensitized halide silver emulsion layer
DE1213240B (en) * 1964-02-13 1966-03-24 Agfa Gevaert Ag Light-sensitive photographic material with at least one optically sensitized halogen silver emulsion layer containing at least one azo dye for the silver dye bleaching process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5409809A (en) * 1992-10-01 1995-04-25 E. I. Du Pont De Nemours And Company Silver halide emulsions stabilized with improved antifoggants

Also Published As

Publication number Publication date
FR2002373A1 (en) 1969-10-17
JPS4751896B1 (en) 1972-12-27
BE728728A (en) 1969-08-21
DE1906952A1 (en) 1969-09-25
DE1906952C2 (en) 1983-04-07

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Legal Events

Date Code Title Description
PS Patent sealed
435 Patent endorsed 'licences of right' on the date specified (sect. 35/1949)
PCNP Patent ceased through non-payment of renewal fee