GB841588A - Improvements in or relating to cyanine dyes - Google Patents
Improvements in or relating to cyanine dyesInfo
- Publication number
- GB841588A GB841588A GB2118457A GB2118457A GB841588A GB 841588 A GB841588 A GB 841588A GB 2118457 A GB2118457 A GB 2118457A GB 2118457 A GB2118457 A GB 2118457A GB 841588 A GB841588 A GB 841588A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- alkyl
- methyl
- residue
- carbon atoms
- 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
- 239000000975 dye Substances 0.000 title abstract 4
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- -1 ketomethylene Chemical class 0.000 abstract 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 2
- KRTLKPFLTASKCG-UHFFFAOYSA-N pyridin-4-ylhydrazine Chemical compound NNC1=CC=NC=C1 KRTLKPFLTASKCG-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- QZOFFMRDIRXGKJ-UHFFFAOYSA-M hydron;4-pyridin-1-ium-1-ylpyridine;dichloride Chemical compound Cl.[Cl-].C1=CC=CC=[N+]1C1=CC=NC=C1 QZOFFMRDIRXGKJ-UHFFFAOYSA-M 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
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
- C09B23/10—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
- C09B23/02—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
- C09B23/14—Styryl dyes
- C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Abstract
1 : 1 : 2 - Trimethyl - 3 : 6 - diazaindene is prepared by refluxing 4-hydrazinopyridine and methyl isopropyl ketone in benzene and removing the water formed by azeotropic distillation. The residue is filtered off and heated with anhydrous zinc chloride, whereupon ammonia is evolved to yield the required product. The product may be quaternized at the 6-N atom, e.g. by boiling with methyl iodide. 4-Hydrazinopyridine is prepared by adding powdered 4-pyridylpyridinium chloride hydrochloride to hydrazine hydrate.ALSO:Methine dyes having one of the general formulae: <FORM:0841588/IV (c)/1> wherein R1, R2, R5 and R6 are alkyl groups of 1 to 4 carbon atoms, R3 is an alkyl group of 1 to 4 carbon atoms, a hydroxyalkyl group or an aralkyl group, R4 is an alkyl group of 1 to 4 carbon atoms or an aralkyl group, m and n are 0 or 1, X is an anion, Z is CH or N, D1 completes a 5- or 6-membered heterocyclic ring, and D2 is the residue of a ketomethylene nucleus, are prepared by condensing of compound of the formula: <FORM:0841588/IV (c)/2> with (1) a cyclammonium quaternary salt having a reactive thioether, thioethervinyl or acetanilidovinyl group, (2) a cyclic ketomethylene compound and an alkyl orthoformate, or (3) a p-dialkylamine-benzaldehyde. Examples are given of the preparation of dyes wherein R1, R2, R3, R4, R5 and R6 are methyl or ethyl groups, D1 completes a benzthiazole nucleus and D2 is the residue of 3-methyl-1-phenyl-5-pyrazolone. According to the Provisional Specification, one of the methine groups in the merocyanine dyes may have an alkyl substituent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2118457A GB841588A (en) | 1957-07-04 | 1957-07-04 | Improvements in or relating to cyanine dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2118457A GB841588A (en) | 1957-07-04 | 1957-07-04 | Improvements in or relating to cyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB841588A true GB841588A (en) | 1960-07-20 |
Family
ID=10158597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2118457A Expired GB841588A (en) | 1957-07-04 | 1957-07-04 | Improvements in or relating to cyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB841588A (en) |
-
1957
- 1957-07-04 GB GB2118457A patent/GB841588A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB870633A (en) | Pentamethincyanines | |
| GB926691A (en) | Improvements in sensitized photographic emulsions and in sensitizing dyes therefor | |
| GB870753A (en) | Improvements in or relating to methine dyes | |
| GB893681A (en) | Improvements in dye-sensitized photographic emulsions | |
| GB1077611A (en) | Spectral sensitisation process | |
| GB792380A (en) | Improvements in photographic sensitizing dyes | |
| GB549202A (en) | Improvements in or relating to dyestuffs and dyestuff intermediates | |
| GB868798A (en) | Improvements in photographic sensitizing dyes | |
| GB841588A (en) | Improvements in or relating to cyanine dyes | |
| GB1093938A (en) | Process for the preparation of cyanine and merocyanine dyes | |
| GB1000196A (en) | Photosensitive compositions including merocyanine dye bases | |
| GB839020A (en) | Improvements in or relating to cyanine and merocyanine dyes | |
| GB1000790A (en) | Improvements in or relating to cyanine dyes and to photographic silver halide emulsions containing cyanine dyes | |
| GB979045A (en) | Polymethine dyes, process of making them and photographic elements containing them | |
| GB782311A (en) | Merocyanine dyes, methods of making them and photographic emulsions containing them | |
| GB899917A (en) | Improvements in or relating to polymethine dyes | |
| GB738258A (en) | Polymethine dyes and process for preparing them | |
| GB871113A (en) | Cyanine bases and undissociated cyanine dyes containing an azaindenyl nucleus | |
| GB811876A (en) | Improvements in or relating to cyanine dyestuffs | |
| GB740770A (en) | Improvements in and relating to polymethine dyes and photographic silver halide emulsions containing them | |
| US2535992A (en) | Thiazolone cyanine dye intermediates | |
| GB845588A (en) | Improvements in or relating to trinuclear cyanine dyes | |
| GB850482A (en) | Improvements in or relating to photographic desensitised emulsions | |
| GB845587A (en) | Improvements in or relating to indoline cyanine dyes | |
| GB843363A (en) | Improvements in or relating to photographic desensitising compounds |