GB610064A - Improvements in methods of making cyanine dyes and in photographic emulsions containing them - Google Patents
Improvements in methods of making cyanine dyes and in photographic emulsions containing themInfo
- Publication number
- GB610064A GB610064A GB3090145A GB3090145A GB610064A GB 610064 A GB610064 A GB 610064A GB 3090145 A GB3090145 A GB 3090145A GB 3090145 A GB3090145 A GB 3090145A GB 610064 A GB610064 A GB 610064A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- benzthiazolylidene
- heating
- iodide
- methylbenzthiazole
- 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
- 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
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Di-2-benzoxazolylmethane is prepared by refluxing together o-aminophenol and ethyl malonate, a stream of CO2 gas being passed through the apparatus. Di-2-benzthiazolylmethane and di-2-benzselenazolylmethane are similarly prepared. 2-Benzthiazolyl-2-quinolylmethane is prepared by refluxing together 2-chlorobenzthiazole and quinaldine. Di - 2 - benzthiazolyl - 2 - quinolyl - methane is obtained as a by-product. 2 - (3 - b - Bromoethyl - 2 - benzthiazolylidene) - methylbenzthiazole is prepared by heating together 2 - (3 - b - hydroxyethyl - 2 - benzthiazolylidene)-methylbenzthiazole and phosphorus tribromide. 2-(3-b -Bromoethyl-2-benzthiazolylidene) - methylquinoline and 2 - (3 - g - bromo - propyl - 2 - benzthiazolylidene) - methylbenzthia - zole are similarly prepared. 2 - (3 - b - Hydroxyethyl - 2 - benzthiazolylidene)-methylbenzthiazole is prepared by heating together di-2-benzthiazolylmethane and ethylene bromohydrin, and rendering alkaline with ammonium hydroxide. 2 - (3 - g - Hydroxy - propyl - 2 - benzthiazolylidene) - methylbenzthia - zole is similarly prepared from di - 2 - benz - thiazolylmethane and trimethylenebromo - hydrin. 2 - (3 - b - Hydroxyethyl - 2 - benzthiazolylidene)-methylquinoline is prepared by refluxing together 2 - methylbenzthiazole b - hydroxyethobromide and 2-methylmercaptoquinoline, and adding triethylamine.ALSO:A cyanine dye of the general formula <FORM:0610064/IV (c)/1> wherein Z and Z1 each represent the nonmetallic atoms necessary to complete a 5- or 6-membered heterocyclic ring, X represents an anion, and n is 2 or 3 is prepared by heating a di-heterocyclylmethane of the general formula <FORM:0610064/IV (c)/2> with an ethylene or propylene arylsulphonate, and then treating the product with an acid-binding agent. The dye may also be prepared by heating an N-bromoethyl or N-bromopropyl cyanine base of the general formula <FORM:0610064/IV (c)/3> The heating may be effected at from 150 DEG to 200 DEG C., and the acid-binding agent may be a trialkylamine, a dialkylamine, an N-alkylpiperidine, sodium carbonate or ammonia. The dye arylsulphonates obtained in the first method may be converted to iodides, bromides, or perchlorates, and the dye bromides obtained in the second process may be converted to iodides or perchlorates. The bromides or iodides may be converted into chlorides by treatment with silver chloride in a phenol. 3 : 31-Ethylenethiacyanine iodide is prepared by heating together di-2-benzthiazolylmethane and ethylene di-p-toluenesulphonate, suspending the product in hot methyl alcohol and adding triethylamine, and adding a hot methyl alcohol solution of sodium iodide. 1 : 11-Ethylene-2 : 11-cyanine iodide, and 3 : 31-ethyleneoxacyanine iodide are similarly prepared, and dyes can be obtained similarly from di-2-benzselenazolylmethane, di-2-(4-thiazolyl)-methane, di-2-(4-phenylthiazolyl) - methane, di - 2 - (5 - methyl - benzoxazole) - methane, 2 - benzthiazolyl - 2 - quinolylmethane and 2 - benzoxazolyl - 2 - benzthiazolylmethane. 3 : 31-Propylenethiacyanine bromide is prepared by heating 2-(3-bromopropyl-2-benzthiazolylidene)-methylbenzthiazole. 3 : 31-Ethylenethiacyanine iodide and 11 : 3-ethylenethia-21-cyanine iodide are similarly prepared.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3090145A GB610064A (en) | 1945-11-17 | 1945-11-17 | Improvements in methods of making cyanine dyes and in photographic emulsions containing them |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3090145A GB610064A (en) | 1945-11-17 | 1945-11-17 | Improvements in methods of making cyanine dyes and in photographic emulsions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
GB610064A true GB610064A (en) | 1948-10-11 |
Family
ID=10314868
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3090145A Expired GB610064A (en) | 1945-11-17 | 1945-11-17 | Improvements in methods of making cyanine dyes and in photographic emulsions containing them |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB610064A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0747448A2 (en) * | 1995-06-07 | 1996-12-11 | Carnegie-Mellon University | Rigidized monomethine cyanine dyes |
US5852191A (en) * | 1995-06-07 | 1998-12-22 | Carnegie Mellon University | Rigidized monomethine cyanines |
US5981747A (en) * | 1995-06-07 | 1999-11-09 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
-
1945
- 1945-11-17 GB GB3090145A patent/GB610064A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0747448A2 (en) * | 1995-06-07 | 1996-12-11 | Carnegie-Mellon University | Rigidized monomethine cyanine dyes |
GB2301832A (en) * | 1995-06-07 | 1996-12-18 | Univ Carnegie Mellon | Rigidized monomethine cyanine dyes by cyclisation of di(heterocyclyl)methane precursors |
EP0747448A3 (en) * | 1995-06-07 | 1997-03-05 | Univ Carnegie Mellon | Rigidized monomethine cyanine dyes |
GB2301832B (en) * | 1995-06-07 | 1998-03-11 | Univ Carnegie Mellon | Rigidized monomethine cyanine dyes |
US5852191A (en) * | 1995-06-07 | 1998-12-22 | Carnegie Mellon University | Rigidized monomethine cyanines |
US5981747A (en) * | 1995-06-07 | 1999-11-09 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
US5986093A (en) * | 1995-06-07 | 1999-11-16 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
US6207464B1 (en) | 1995-06-07 | 2001-03-27 | Carnegie Mellon University | Rigidized monomethine cyanines |
US6277984B1 (en) | 1995-06-07 | 2001-08-21 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
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