GB513471A - Improvements in and relating to the production of dyes and their use for sensitizing photographic silver halide emulsions - Google Patents
Improvements in and relating to the production of dyes and their use for sensitizing photographic silver halide emulsionsInfo
- Publication number
- GB513471A GB513471A GB7273/38A GB727338A GB513471A GB 513471 A GB513471 A GB 513471A GB 7273/38 A GB7273/38 A GB 7273/38A GB 727338 A GB727338 A GB 727338A GB 513471 A GB513471 A GB 513471A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethiodide
- ethyl
- alkyl
- methyl
- salt
- 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
-
- 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
- G03C1/16—Methine and polymethine dyes with an odd number of CH groups with one CH group
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
513,471. Sensitizing dyes. DU PONT FILM MANUFACTURING CORPORATION. March 8, 1938, No. 7273. Convention date, March 9, 1937. [Class 2 (iii)] [Also in Group XX] Dyes suitable for sensitizing photographic silver halide emulsions are made by reacting a bisazole dithioether alkly quarternary salt of the formula [Y & Z=O, S or Se, R=aryl, X=an acid radical] with an alkyl quarternary salt of a heterocyclic nitrogen compound containing a reactive alkyl group in (alpha- or gamma-position to the nitrogen atom. Generally only one thioalkyl group reacts but in some cases by-products may be formed due possibly to the reaction of both thioalkyl groups. In the examples (1) the dimercaptobisthiazole from p-phenylenidiamine is treated with dimethyl sulphur, the dithioether obtained converted into a quarternary salt by heating with ethyl p-toluene sulphonate or diethylsulphate &c. The salt condensed in alcohol with 2-methylbenzthiazole ethyl iodide in presence of sodium acetate, (2)-(5) the dithioether ethyl sulphate of (1) is condensed with lepidine ethiodide, #-naphthoquinaldine ethiodide, 2-methylbenzselenazole ethiodide or 2-ethyl-5-methylbenzselenazole ethiodide, (6)-(8), (10)-(13) the 2:2'-dimercaptan of tolylbisthiazole from 1-methyl-2:4-diaminobenzene is methylated as above, converted into the ethyl p-toluenesulphonate or ethyl sulphate and condensed with 2-methylbenzthiazole ethiodide, 2-methylbenzselenazole ethiodide, quinaldine ethiodide, lepidine ethiodide, #-naphthaquinaldine ethiodide, 2-metbyl- #-naphthathiazole ethyl sulphate or 2-methylbenzoxazole ethiodide, (9), (14)-(18) the 2:2<1>-dimethylmercaptobenzbisthiazole from m-phenylene diamine is heated with diethyl sulphate and the quaternary salt condensed with 2:5-dimethylbenzselenazole ethiodide, 2 - methyl - benzthiazole ethiodide, 2-ethyl-5-methylbenzthiazole ethiodide, quinaldine ethiodide, 2- methylbenzoxazole ethiodide or lepidine ethiodide. Other starting materials specied are 6- methyl-, 6-ethoxy- or 7:8-benzlepidine; alkyl, halogen or alkoxy derivatives of 2-methylquinoline ; 2:5-dimethyl-benzthiazole or benzsolenazole, 2-ethyl-5-methyl-benzthiazole or benselenazole and other derivatives containing alkyl, alkoxy, halogen, or dialkylamino ; 2-methylalpha-naphthaselenazole ; 2:4 - dimethyl - thiazole. oxazole or selenazole, 2-methyl-4-phenyl-or 4:5- diphenylthiazole ; 2:3:3-trimethylindolenine. The bisazole dithiother alkyl quaternary salts may be made (1) by heating an aromatic diamine with carbon disulphide and sulphur to give the dimercaptobisthiazole, alkylating, and heating with an alkyl salt, (2) by treating o-o<1> diaminodiselenophenols or o:o<1>-diaminodihydroxybenzenes with thiophosyene to form the corresponding 2:2<1>-dimercapto-benzolisselenazoles or oxazoles which are converted into the thioethers by heating with alkyl sulphates ; thus, 2:5-diaminohydroquinone when heated with thiophosgene gives 2:2<1>-dimercaptobenzobisoxazole. Specifications 424,559, and 464,852 [both in Group XX] are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US513471XA | 1937-03-09 | 1937-03-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB513471A true GB513471A (en) | 1939-10-13 |
Family
ID=21970746
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7273/38A Expired GB513471A (en) | 1937-03-09 | 1938-03-08 | Improvements in and relating to the production of dyes and their use for sensitizing photographic silver halide emulsions |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB513471A (en) |
-
1938
- 1938-03-08 GB GB7273/38A patent/GB513471A/en not_active Expired
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