GB1087315A - Benzimidazole derivatives and process for the preparation thereof - Google Patents

Benzimidazole derivatives and process for the preparation thereof

Info

Publication number
GB1087315A
GB1087315A GB4714764A GB4714764A GB1087315A GB 1087315 A GB1087315 A GB 1087315A GB 4714764 A GB4714764 A GB 4714764A GB 4714764 A GB4714764 A GB 4714764A GB 1087315 A GB1087315 A GB 1087315A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compounds
substituted
dyes
difluoroacetanilide
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
GB4714764A
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.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
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 Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Publication of GB1087315A publication Critical patent/GB1087315A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon 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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14—Radicals substituted by nitrogen 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
    • 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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • G03C1/14—Methine and polymethine dyes with an odd number of CH groups
    • G03C1/18—Methine and polymethine dyes with an odd number of CH groups with three CH groups
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings

Abstract

Cyanine and merocyanine dyes are prepared by condensing a compound of the formula <FORM:1087315/C4-C5/1> wherein R1 represents an alkyl, substituted alkyl, aralkyl or substituted aralkyl group, X represents an acid anion and R2 represents a group known in cyanine dye chemistry, e.g. an alkyl, substituted alkyl, allyl, aryl or substituted phenyl group with a variety of heterocyclic compounds. Examples 1-5 describe the preparation of specific carbocyanine dyes. Styryl dyes are prepared by condensing the above benzimidazolium salts with a p-dialkylaminobenzaldehyde, preferably in the presence of acetic anhydride.ALSO:The invention comprises benzimidazole derivatives of the formula <FORM:1087315/C2/1> wherein R1 represents an alkyl, substituted alkyl, aralkyl or substituted aralkyl group. The compounds are prepared by the reduction and cyclisation of 2 - nitro - 4,5 - difluoroacetanilide with hydrogen and Raney nickel in the presence of acetic acid, followed by alkylation of the resulting 2-methyl-5,6-difluorobenzimidazole. The compounds are used in the synthesis of dyes (see Division C4). Examples relate to compounds in which R1 is a methyl or ethyl group. 2 - Nitro - 4,5 - difluoroacetanilide may be made by nitrating 1,2-difluorobenzene to 1,2-difluoro-4 -nitrobenzene, reducing this to the corresponding amine, which is then acetylated to give 4,5-difluoroacetanilide which on nitration gives the 2-nitro compound.
GB4714764A 1963-11-27 1964-11-19 Benzimidazole derivatives and process for the preparation thereof Expired GB1087315A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE43184 1963-11-27

Publications (1)

Publication Number Publication Date
GB1087315A true GB1087315A (en) 1967-10-18

Family

ID=3840395

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4714764A Expired GB1087315A (en) 1963-11-27 1964-11-19 Benzimidazole derivatives and process for the preparation thereof

Country Status (1)

Country Link
GB (1) GB1087315A (en)

Similar Documents

Publication Publication Date Title
ES383503A1 (en) 1,1,1-trichloro-2-amido-2-amino-ethanes
GB1087315A (en) Benzimidazole derivatives and process for the preparation thereof
US3860583A (en) Indolenine dyestuffs
GB764626A (en) Improvements in sensitized photographic emulsions
GB1062950A (en) Trimethine dyes
US2422029A (en) Bicyclic compound containing a diphenylamine nucleus
GB776050A (en) Improvements in carbocyanine dyes, processes of preparing them and photographic emulsions containing them
GB1102439A (en) Azo dyestuffs containing a quaternised triazolium ring and process for their production
GB726148A (en) New carbocyanine dyes, methods for making them and photographic silver halide emulsions containing them
GB738258A (en) Polymethine dyes and process for preparing them
GB816014A (en) Process of making diaryloxyazole quaternary salts, diaryloxazole quaternary salts made thereby, cyanine dyes containing a diaryloxazole nucleus made from such salts and photographic silver halide emulsions containing such dyes
GB812924A (en) Improvements in sensitising dyes for photographic silver halide emulsions
US2647116A (en) Cyanine dye salts
GB772347A (en) Improvements in cyanine dyes, processes of preparing them and photographic emulsionscontaining them
GB1343090A (en) Coumarine derivatives their preparation and use as brighteners
GB801275A (en) New photo-sensitizing dyestuffs and their manufacture and products containing them
GB1001741A (en) New monazo dyes
US2917516A (en) Method of making thiazole or oxazole quaternary salts
US2508324A (en) Heterocyclic nitrogenous cyanine dyes containing a new group added to the nitrogen atom thereof
GB922093A (en) Polymethine dyes and photographic emulsions containing them
GB1055984A (en) Cationic phthalocyanine and azo dyestuffs and process for their manufacture
GB845588A (en) Improvements in or relating to trinuclear cyanine dyes
US2647115A (en) Cyanine dyes
SU92204A1 (en) Method for sensitization of halo-silver photoemulsions
GB837471A (en) New basic heterocyclic diazacyanine dyestuffs and their production