GB981453A - Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions - Google Patents

Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions

Info

Publication number
GB981453A
GB981453A GB1923064A GB1923064A GB981453A GB 981453 A GB981453 A GB 981453A GB 1923064 A GB1923064 A GB 1923064A GB 1923064 A GB1923064 A GB 1923064A GB 981453 A GB981453 A GB 981453A
Authority
GB
United Kingdom
Prior art keywords
ethyl
methyl
nitro
heating
benzimidazole
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
GB1923064A
Inventor
Henri Depoorter
Marcel Jan Libeer
Gerrit Godfried Van Mierlo
Jean Marie Nys
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
Priority to GB1923064A priority Critical patent/GB981453A/en
Priority claimed from GB34641/59A external-priority patent/GB955962A/en
Priority claimed from GB3527560A external-priority patent/GB975504A/en
Publication of GB981453A publication Critical patent/GB981453A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • 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
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • 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
    • 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
    • G03C1/28—Sensitivity-increasing substances together with supersensitising substances
    • G03C1/29—Sensitivity-increasing substances together with supersensitising substances the supersensitising mixture being solely composed of dyes ; Combination of dyes, even if the supersensitising effect is not explicitly disclosed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Abstract

1 - Ethyl - 2 - methyl - 5 - carboxy - benzimidazole is prepared by heating 3-nitro-4-chlorobenzoic acid with ethylamine to give 3-nitro-4-ethylamino-benzoic acid, reducing the nitro-group and refluxing the product with acetic acid and hydrochloric acid to effect ring closure. The product is quaternized by heating with ethyl toluene sulphonate. 1-Ethyl-2-methyl-7-carboxy-benzimidazol is similarly prepared from 2 - bromo - 3 - nitro - benzoic acid, and quaternized by heating with methyl iodide. 1 - Ethyl - 2 - methyl - 7 - carbethoxy - benzimidazole, prepared as described in Example 13 of Specification 955,961, is quaternized by heating with ethyl iodide, ethylene bromohydrine or N-acetyl-4-bromobutane sulphonamide. Specifications 904,332 and 955,962 also are referred to.ALSO:Cyanine and merocyanine dyes are described which contain a benzimidazole nucleus having a 5- or 7-carboxyl or a 7-carbethoxy substituent. Examples are given of the preparation of carbocyanine dyes by condensing the appropriately substituted 2-methyl-benzimidazolium salt with ethyl ortho formate to give a symmetrical dye, or with heterocyclic bases (such as benzthiazoline or benzoxazoline) having a reactive b -phenylimino-ethylidene group or with cyclammonium salts such as 2-(b -acetanilidovinyl) - 3 - ethyl - thiazolinium bromide and 1:3 - diethyl - 2 - {b - (p - tolusulpho - anilido)-vinyl} - 5:6 - dichlorobenzimidazolium chloride to give unsymmetrical dyes. A merocyanine dye is obtained by refluxing 1:3-diethyl-2-methyl - 7 - carbethoxy - benzimidazolium iodide with 3 - ethyl - 5 - acetanilidomethylidene rhodanine. The 1-nitrogen atom of the benzimidazole nucleus may carry a b -acetoxyethyl or 4 - (N - acetylsulphonamido) - butyl substituent. Specifications 904,332, 955,961 and 955,962 also are referred to.
GB1923064A 1959-10-13 1959-10-13 Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions Expired GB981453A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1923064A GB981453A (en) 1959-10-13 1959-10-13 Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB34641/59A GB955962A (en) 1959-10-13 1959-10-13 Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions
GB1923064A GB981453A (en) 1959-10-13 1959-10-13 Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions
GB3527560A GB975504A (en) 1959-10-13 1959-10-13 Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions

Publications (1)

Publication Number Publication Date
GB981453A true GB981453A (en) 1965-01-27

Family

ID=27257726

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1923064A Expired GB981453A (en) 1959-10-13 1959-10-13 Improvements in or relating to new sensitizing dyes and sensitized photographic emulsions

Country Status (1)

Country Link
GB (1) GB981453A (en)

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