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 emulsionsInfo
- 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
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.
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) |
-
1959
- 1959-10-13 GB GB1923064A patent/GB981453A/en not_active Expired
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