GB1020295A - Cyanine dyes production and use - Google Patents
Cyanine dyes production and useInfo
- Publication number
- GB1020295A GB1020295A GB23256/63A GB2325663A GB1020295A GB 1020295 A GB1020295 A GB 1020295A GB 23256/63 A GB23256/63 A GB 23256/63A GB 2325663 A GB2325663 A GB 2325663A GB 1020295 A GB1020295 A GB 1020295A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- prepared
- ethyl
- benzimidazole
- betaine
- 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 1
- 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
- -1 trifluoromethylsulphonyl group Chemical group 0.000 abstract 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 abstract 3
- 229960003237 betaine Drugs 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 abstract 1
- LXNGDRGLRRDJOB-UHFFFAOYSA-N 1-ethyl-2-methyl-5-(trifluoromethyl)benzimidazole Chemical compound FC(F)(F)C1=CC=C2N(CC)C(C)=NC2=C1 LXNGDRGLRRDJOB-UHFFFAOYSA-N 0.000 abstract 1
- DLHWKJDYXPNWAI-UHFFFAOYSA-N 2,2,2-trichloro-1-ethoxyethanol Chemical compound CCOC(O)C(Cl)(Cl)Cl DLHWKJDYXPNWAI-UHFFFAOYSA-N 0.000 abstract 1
- CBSSBEXUJFBWEM-UHFFFAOYSA-N CCC(C(C)C(C)S([O-])(=O)=O)[N+]1=CNC2=C1C=CC(S(C(F)(F)F)(=O)=O)=C2 Chemical compound CCC(C(C)C(C)S([O-])(=O)=O)[N+]1=CNC2=C1C=CC(S(C(F)(F)F)(=O)=O)=C2 CBSSBEXUJFBWEM-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000000298 carbocyanine Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- MLCWLZDBWZUMBM-UHFFFAOYSA-M sodium;3-iodopropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCI MLCWLZDBWZUMBM-UHFFFAOYSA-M 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C09B23/02—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
-
- 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
- G03C1/18—Methine and polymethine dyes with an odd number of CH groups with three CH groups
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Coloring (AREA)
Abstract
Benzimidazole carbocyanine dyes having the general formula <FORM:1020295/C4-C5/1> wherein R1 is an alkyl, aryl, substituted aryl or aralkyl group, R2 is a trifluoromethyl or trifluoromethylsulphonyl group and n is 1 to 6, are prepared by reacting a 1-sulphoalkyl-2-methyl-benzimidazolium betaine with an orthoformic acid ester in an inert solvent or with a chloral alcoholate in an alcoholic alkali metal alkoxide solution.ALSO:1 - Ethyl - 2 - methyl - 3 - sulphobutyl - 5 -trifluoromethylbenzimidazolium betaine is prepared by heating 1-ethyl-2-methyl-5-trifluoromethyl benzimidazole with butane sultone on an oil bath. The corresponding 1-methyl and 1-phenyl betaines, and 1 - ethyl - 2 - methyl - 3 - sulphobutyl - 5 - trifluoromethylsulphonyl benzimidazolium betaine are similarly prepared from the corresponding benzimidazole bases. 1 - Ethyl - 2 - methyl - 3 (3 - sulphopropyl) - 5-trifluoromethyl benzimidazolium iodide sodium salt is prepared by heating the above benzimidazole with 3-iodopropane-sulphonic acid sodium salt (prepared from sodium iodide and 1,3-propane sultone).
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23256/63A GB1020295A (en) | 1963-06-11 | 1963-06-11 | Cyanine dyes production and use |
| CH743364A CH420446A (en) | 1963-06-11 | 1964-06-08 | Process for the preparation of cyanine dyes, and their applications |
| FR977412A FR1397876A (en) | 1963-06-11 | 1964-06-08 | Cyanine dyes, their preparation and applications |
| BE648981A BE648981A (en) | 1963-06-11 | 1964-06-08 | |
| NL6406516A NL6406516A (en) | 1963-06-11 | 1964-06-09 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23256/63A GB1020295A (en) | 1963-06-11 | 1963-06-11 | Cyanine dyes production and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1020295A true GB1020295A (en) | 1966-02-16 |
Family
ID=10192705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23256/63A Expired GB1020295A (en) | 1963-06-11 | 1963-06-11 | Cyanine dyes production and use |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE648981A (en) |
| CH (1) | CH420446A (en) |
| FR (1) | FR1397876A (en) |
| GB (1) | GB1020295A (en) |
| NL (1) | NL6406516A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013041117A1 (en) * | 2011-09-23 | 2013-03-28 | Illumina Cambrigde Ltd. | Dyes for labelling molecular ligands |
| US8809551B1 (en) | 2013-03-08 | 2014-08-19 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US9309409B2 (en) | 2014-05-07 | 2016-04-12 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US10239909B2 (en) | 2015-05-22 | 2019-03-26 | Illumina Cambridge Limited | Polymethine compounds with long stokes shifts and their use as fluorescent labels |
| US10982261B2 (en) | 2015-09-25 | 2021-04-20 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210014A (en) * | 1991-03-28 | 1993-05-11 | Eastman Kodak Company | Mid-green sensitizing dyes for photographic materials |
| US5196299A (en) * | 1991-03-28 | 1993-03-23 | Eastman Kodak Company | Tabular grain emulsion containing radiographic elements exhibiting reduced dye stain |
-
1963
- 1963-06-11 GB GB23256/63A patent/GB1020295A/en not_active Expired
-
1964
- 1964-06-08 FR FR977412A patent/FR1397876A/en not_active Expired
- 1964-06-08 CH CH743364A patent/CH420446A/en unknown
- 1964-06-08 BE BE648981A patent/BE648981A/xx unknown
- 1964-06-09 NL NL6406516A patent/NL6406516A/xx unknown
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9376568B2 (en) | 2011-09-23 | 2016-06-28 | Illumina Cambridge Limited | Dyes for labelling molecular ligands |
| US9085698B2 (en) | 2011-09-23 | 2015-07-21 | Illumina Cambridge Limited | Dyes for labelling molecular ligands |
| WO2013041117A1 (en) * | 2011-09-23 | 2013-03-28 | Illumina Cambrigde Ltd. | Dyes for labelling molecular ligands |
| US9738786B2 (en) | 2011-09-23 | 2017-08-22 | Illumina Cambridge Limited | Dyes for labelling molecular ligands |
| US8809551B1 (en) | 2013-03-08 | 2014-08-19 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US8993784B2 (en) | 2013-03-08 | 2015-03-31 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US9156987B2 (en) | 2013-03-08 | 2015-10-13 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US9309409B2 (en) | 2014-05-07 | 2016-04-12 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US10144967B2 (en) | 2014-05-07 | 2018-12-04 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US10239909B2 (en) | 2015-05-22 | 2019-03-26 | Illumina Cambridge Limited | Polymethine compounds with long stokes shifts and their use as fluorescent labels |
| US10982261B2 (en) | 2015-09-25 | 2021-04-20 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US11530439B2 (en) | 2015-09-25 | 2022-12-20 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
| US11981955B2 (en) | 2015-09-25 | 2024-05-14 | Illumina Cambridge Limited | Polymethine compounds and their use as fluorescent labels |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6406516A (en) | 1964-12-14 |
| BE648981A (en) | 1964-10-01 |
| FR1397876A (en) | 1965-04-30 |
| CH420446A (en) | 1966-09-15 |
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