GB811876A - Improvements in or relating to cyanine dyestuffs - Google Patents
Improvements in or relating to cyanine dyestuffsInfo
- Publication number
- GB811876A GB811876A GB2441556A GB2441556A GB811876A GB 811876 A GB811876 A GB 811876A GB 2441556 A GB2441556 A GB 2441556A GB 2441556 A GB2441556 A GB 2441556A GB 811876 A GB811876 A GB 811876A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- prepared
- alkyl
- methyl
- heterocyclic
- 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
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical group CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 abstract 1
- CMIWIRFHWMTUFP-UHFFFAOYSA-N 4-phenyl-4,5-dihydro-1,3-thiazole Chemical compound C1SC=NC1C1=CC=CC=C1 CMIWIRFHWMTUFP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 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
- C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
-
- 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)
- Indole Compounds (AREA)
Abstract
3 : 3 - Dimethyl - 2 - mercapto - indolenine is prepared by heating 3 : 3-dimethyl-oxindole with phosphorus pentasulphide at 160-165 DEG C., and extracting with benzene. 3 : 3 - Dimethyl - 2 - methylthio - indolenine is prepared by dissolving the 2-mercapto compound in aqueous caustic soda, cooling in ice and adding dimethyl sulphate.ALSO:Cyanine dye bases having one of the general formul <FORM:0811876/IV (c)/1> and <FORM:0811876/IV (c)/2> wherein R2 is alkyl or hydroxyalkyl, R3 is alkyl aryl, substituted aryl or aralkyl, Z is -CH= or -N=, m is 0 or 1 and D1 and D2 complete heterocyclic nuclei, are prepared by reacting a 3 : 3-dimethylindolenine base having an alkylthio or aralkylthio group in the 2-position with a quaternary heterocyclic salt having a reactive a - or g -methyl group or with a heterocyclic hetomethylene compound. In the examples, D1 completes a benzthiazole, benzoxazole, benzselenazole, 1 : 3 : 3-trimethylindolenine, 4-phenylthiazoline or quinoline ring, D2 completes a rhodanine or 3-methyl-5-pyrazolone ring, R2 is methyl or ethyl and R3 is ethyl or phenyl. It is stated that R3 may be phenyl substituted by one or two halogen, alkyl or alkoxy groups.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2441556A GB811876A (en) | 1956-08-09 | 1956-08-09 | Improvements in or relating to cyanine dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2441556A GB811876A (en) | 1956-08-09 | 1956-08-09 | Improvements in or relating to cyanine dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB811876A true GB811876A (en) | 1959-04-15 |
Family
ID=10211377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2441556A Expired GB811876A (en) | 1956-08-09 | 1956-08-09 | Improvements in or relating to cyanine dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB811876A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3073820A (en) * | 1960-08-10 | 1963-01-15 | Arnold F Plue | 2-pyrazolinyl-vinyl-1, 3, 3 trimethyl indolenines |
| EP1142961A2 (en) * | 2000-04-06 | 2001-10-10 | Fuji Photo Film Co., Ltd. | Dye complex and optical information recording medium |
| US7402375B2 (en) * | 1999-12-17 | 2008-07-22 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Cyanine dyes |
| US7408062B2 (en) | 1997-12-17 | 2008-08-05 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
-
1956
- 1956-08-09 GB GB2441556A patent/GB811876A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3073820A (en) * | 1960-08-10 | 1963-01-15 | Arnold F Plue | 2-pyrazolinyl-vinyl-1, 3, 3 trimethyl indolenines |
| US7408062B2 (en) | 1997-12-17 | 2008-08-05 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
| US7964361B2 (en) | 1997-12-17 | 2011-06-21 | Carnegie Mellon University | Rigidized trimethine cyanine dyes |
| US7402375B2 (en) * | 1999-12-17 | 2008-07-22 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Cyanine dyes |
| EP1142961A2 (en) * | 2000-04-06 | 2001-10-10 | Fuji Photo Film Co., Ltd. | Dye complex and optical information recording medium |
| EP1142961A3 (en) * | 2000-04-06 | 2004-05-26 | Fuji Photo Film Co., Ltd. | Dye complex and optical information recording medium |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1110577A (en) | Dyes | |
| GB792380A (en) | Improvements in photographic sensitizing dyes | |
| GB811876A (en) | Improvements in or relating to cyanine dyestuffs | |
| GB862443A (en) | Improvements in dye-sensitized photographic emulsions | |
| GB609033A (en) | Cyanine dyes containing a carbonyl or thiocarbonyl substituent in the methine-chain and photographic silver-halide emulsions senzitized therewith | |
| GB756226A (en) | Trinuclear polymethine dyes containing a pyrryl, indolyl or pyrrocolyl nucleus and photographic emulsions containing such dyes | |
| GB1093938A (en) | Process for the preparation of cyanine and merocyanine dyes | |
| GB979045A (en) | Polymethine dyes, process of making them and photographic elements containing them | |
| GB1000196A (en) | Photosensitive compositions including merocyanine dye bases | |
| GB738258A (en) | Polymethine dyes and process for preparing them | |
| GB717858A (en) | Improvements in or relating to cyanine dyes | |
| GB874809A (en) | Improvements in or relating to dyestuffs | |
| GB740770A (en) | Improvements in and relating to polymethine dyes and photographic silver halide emulsions containing them | |
| GB772347A (en) | Improvements in cyanine dyes, processes of preparing them and photographic emulsionscontaining them | |
| GB855686A (en) | Cyanine dyes and silver halide emulsions sensitised therewith | |
| GB681736A (en) | Improvements in or relating to dyestuffs and photographic emulsions containing the same | |
| GB899917A (en) | Improvements in or relating to polymethine dyes | |
| GB1102891A (en) | Process for the preparation of heterocyclammonium betaines | |
| GB829790A (en) | Improvements in or relating to merocyanine dyes | |
| US2441530A (en) | Merocarbocyanine dyes containing a cycloalkyl group on the dimethine chain | |
| GB641805A (en) | Process of producing cyanine dyes | |
| GB1012958A (en) | Production of cyanine dyes | |
| GB829644A (en) | Improvements in or relating to merocyanine dyes | |
| GB719238A (en) | Improvements in or relating to meso-substituted carbo-cyanine dyes | |
| GB834751A (en) | New photographic sensitisers |