GB344409A - Improvements in and relating to the manufacture of intermediates and dyes from heterocyclic nitrogen compounds - Google Patents
Improvements in and relating to the manufacture of intermediates and dyes from heterocyclic nitrogen compoundsInfo
- Publication number
- GB344409A GB344409A GB3349329A GB3349329A GB344409A GB 344409 A GB344409 A GB 344409A GB 3349329 A GB3349329 A GB 3349329A GB 3349329 A GB3349329 A GB 3349329A GB 344409 A GB344409 A GB 344409A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diphenylformamidine
- acetic anhydride
- condensing
- product
- intermediates
- 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
- C09B23/06—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Indole Compounds (AREA)
- Coloring (AREA)
Abstract
Intermediates for polymethine dyestuffs are obtained by the interaction of equimolecular quantities of a diarylformamidine with a cyclic ammonium compound having a reactive methyl group or a methylene base thereof, at least one molecular proportion of an acid being present either in the free state or combined with one or both of the reacting compounds. Polymethine dyestuffs are obtained when two molecular proportions of the cyclic ammonium compound having a reactive methyl group or the methylene base thereof are reacted with one molecular proportion of the diarylformamidine. In examples: (1) 2 : 3 : 3-trimethylindoleninemethiodide is condensed with diphenylformamidine in the presence of acetic anhydride; (2) the product of example (1), which is probably aceto-2-anilidovinyl-3 : 31-dimethylindoleninemethiodide is hydrolized by means of concentrated hydrochloric acid whereby the acetyl group is removed: (3) the product of example (2) is prepared directly by condensing 2 : 3 : 3-trimethylindoleninemethiodide with diphenylformamidine: (4) 2-o -acetanilidovinylbenzthiazole ethiodide, and the corresponding dyestuff 1 : 11-diethylcarbothiocyanine iodide are obtained by condensing diphenylformamidine with 2-methylbenzothiazole ethiodide in the presence of acetic anhydride: (5) 2-o -acetanilidovinylbenzoxazolethiodide is obtained by condensing diphenylformamidine with 2-methylbenzoxazole: (6) quinaldineethiodide is condensed with diphenylformamidine to give both the intermediate and the corresponding dyestuff. In the latter case the condensation is effected in the presence of acetic anhydride and sodium acetate: (7) the dyestuff 1 : 3 : 3 : 11 : 31 : 31-hexamethylindocarbocyaninechloride is prepared (a) by condensing 1 : 3 : 3-trimethyl-2-methyleneindoline with diphenylformamidine in the presence of acetic anhydride and crystallizing the product from a hydrochloric acid solution, and (b) by heating 1 : 3 : 3-trimethyl-2-methyleneindoline with diphenylformamidinehydrochloride alone or in the presence of acetic anhydride. Diarylformamidines also specified are p : p1-dichlordiphenylformamidine and di-p-tolylformamidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3349329A GB344409A (en) | 1929-11-04 | 1929-11-04 | Improvements in and relating to the manufacture of intermediates and dyes from heterocyclic nitrogen compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3349329A GB344409A (en) | 1929-11-04 | 1929-11-04 | Improvements in and relating to the manufacture of intermediates and dyes from heterocyclic nitrogen compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB344409A true GB344409A (en) | 1931-03-04 |
Family
ID=10353682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3349329A Expired GB344409A (en) | 1929-11-04 | 1929-11-04 | Improvements in and relating to the manufacture of intermediates and dyes from heterocyclic nitrogen compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB344409A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500128A (en) * | 1950-03-07 | Process fob preparing cyanine dye | ||
| US2500127A (en) * | 1945-01-11 | 1950-03-07 | Eastman Kodak Co | Process for preparing cyclammonium quaternary salts containing an nu-substituted beta-aminovinyl group |
-
1929
- 1929-11-04 GB GB3349329A patent/GB344409A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500128A (en) * | 1950-03-07 | Process fob preparing cyanine dye | ||
| US2500127A (en) * | 1945-01-11 | 1950-03-07 | Eastman Kodak Co | Process for preparing cyclammonium quaternary salts containing an nu-substituted beta-aminovinyl group |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB344409A (en) | Improvements in and relating to the manufacture of intermediates and dyes from heterocyclic nitrogen compounds | |
| US2126852A (en) | Carbocyanine dyestuffs and a process of preparing them | |
| US2156464A (en) | Production of polymethin dyestuffs | |
| US2481464A (en) | Photographic emulsions containing nu-aryloxy-, arylthio-and arylselenoalkyl cyanine dyes | |
| US2638473A (en) | Methine dyestuffs | |
| US2334711A (en) | Ctanine dyestdff intermediates | |
| GB487051A (en) | Improvements in or relating to dyestuffs | |
| US2106383A (en) | Manufacture of carbocyanine dyes | |
| GB615205A (en) | Improvements in and relating to the manufacture of dyes and photographic emulsions sensitised therewith | |
| GB355693A (en) | Manufacture of intermediates and dyes from heterocyclic nitrogen compounds | |
| GB512477A (en) | Manufacture of polymethine dyestuffs | |
| US2504615A (en) | Photographic emulsions containing nu-aryloxy-, arylthio-, and arylselenoalkyl cyanine dyes | |
| US2734901A (en) | Process of preparing evdotlum | |
| GB509927A (en) | Manufacture of dyestuffs | |
| GB531489A (en) | Improvements in the manufacture and production of watersoluble basic dyestuffs | |
| GB512470A (en) | Manufacture of polymethine dyestuffs | |
| GB434234A (en) | Manufacture of unsymmetrical pentacarbocyanine dyestuffs | |
| GB466097A (en) | Improvements in the manufacture of dyes | |
| US2263757A (en) | Ketone dye and process for preparing it | |
| US2573555A (en) | Method for making methine dyestuffs | |
| US2575373A (en) | Acyloxy polymethine dte | |
| US2535994A (en) | Process of preparing trinuclear cyanine dyes containing a terminal 5-and 6-membered heterocyclic ring system | |
| GB485623A (en) | Manufacture of polymethine dyestuffs | |
| GB441624A (en) | Manufacture and application of polymethine dyestuffs and intermediate products | |
| US2553503A (en) | Tetranuclear merocyanine sensitizing dyes from bithiazoles |