GB848016A - Improvements in or relating to cyanine dyes - Google Patents
Improvements in or relating to cyanine dyesInfo
- Publication number
- GB848016A GB848016A GB2201257A GB2201257A GB848016A GB 848016 A GB848016 A GB 848016A GB 2201257 A GB2201257 A GB 2201257A GB 2201257 A GB2201257 A GB 2201257A GB 848016 A GB848016 A GB 848016A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiazine
- prepared
- quaternary salt
- alkyl
- group
- 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 abstract 3
- MSTFRUQNYRRUKZ-UHFFFAOYSA-N 5,6-dihydro-2h-thiazine Chemical compound C1CC=CNS1 MSTFRUQNYRRUKZ-UHFFFAOYSA-N 0.000 abstract 5
- 150000003839 salts Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- -1 ketomethylene Chemical class 0.000 abstract 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-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
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 abstract 1
- VYDRCHNHWXHJSQ-UHFFFAOYSA-N 3-sulfanylidene-1,2,4-oxathiazolidin-5-one Chemical compound S1C(=S)NC(=O)O1 VYDRCHNHWXHJSQ-UHFFFAOYSA-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
- 150000001450 anions Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000000298 carbocyanine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- ADZBLCRDWZGXAI-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)acetamide Chemical compound CC(=O)CC(C)(C)NC(C)=O ADZBLCRDWZGXAI-UHFFFAOYSA-N 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
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=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
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
2 : 4 : 4 : 6-Tetramethyl-4H-1 : 3-thiazine is prepared by mixing N-acetyldiacetonamine and phosphorus pentasulphide and then heating in vacuum on an oil bath. The product may be quaternized with methyl or ethyl iodide. 2-Methylmercapto-4 : 4 : 6-trimethyl-4H-1 : 3-thiazine is prepared by shaking 4 : 4 : 6-trimethyl-2-mercapto-4H-1 : 3-thiazine in aqueous sodium hydroxide with methyltiodide. The product may be quaternized by heating in a sealed tube with methyl iodide. Specification 839,020 is referred to.ALSO:Cyanine dyes having one of the general formula: <FORM:0848016/IV (c)/1> wherein Ra and Rb are alkyl groups of 1 to 5 carbon atoms, m and n are 0 or 1, D1 completes a 5- or 6- membered heterocyclic ring system, D2 is the residue of a ketomethylene nucleus and X is an anion, are prepared by reacting a quaternary salt of a 2; 4; 4; 6-tetramethyl -4H -1; 3-thiazine with a quaternary salt of a heterocyclic nitrogen compound having a reactive a - or g -thioether, thioethervinyl or acetanilidovinyl group, or with a compound of the formula: <FORM:0848016/IV (c)/2> where R is an alkyl group of 1 to 5 carbon atoms. Alternatively, cyanine dyes where m=0 may be prepared by reacting a quaternary salt of the formula: <FORM:0848016/IV (c)/3> (where Rd is an alkyl or aralkyl group) with a quaternary salt of a heterocyclic nitrogen compound having a reactive a - or g -methyl group. Symmetrical carbocyanine dyes where m=1 may be prepared by reacting two moles of a 2; 4; 4; 6-tetramethyl-4H-1; 3-thiazine quaternary salt with 1 mole of an alkyl orthoformate. D1 may complete a benzthiazole, benzoxazole, quinoline, indolenine, pyrroline or 1 : 3 : 4-thiadiazole (e.g. 5-methylthio -3- methyl -1; 3; 4-thiadiazole) nucleus and D2 may be the residue of rhodanine, oxarhodanine, oxazolone, 5-pyrazolone or thiohydantoin. According to the Provisional Specification, one methine group in the merocarbocyanine dyes may have an alkyl substituent and D, may complete a quinazoline nucleus. Specification 839,020 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2201257A GB848016A (en) | 1957-07-11 | 1957-07-11 | Improvements in or relating to cyanine dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2201257A GB848016A (en) | 1957-07-11 | 1957-07-11 | Improvements in or relating to cyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB848016A true GB848016A (en) | 1960-09-14 |
Family
ID=10172506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2201257A Expired GB848016A (en) | 1957-07-11 | 1957-07-11 | Improvements in or relating to cyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB848016A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002080159A1 (en) * | 2001-03-28 | 2002-10-10 | Bayer Aktiengesellschaft | Optical data carrier that contains a cyanine dye as the light-absorbing compound in the information layer |
-
1957
- 1957-07-11 GB GB2201257A patent/GB848016A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002080159A1 (en) * | 2001-03-28 | 2002-10-10 | Bayer Aktiengesellschaft | Optical data carrier that contains a cyanine dye as the light-absorbing compound in the information layer |
| US6835725B2 (en) | 2001-03-28 | 2004-12-28 | Bayer Aktiengesellschaft | Optical data carrier comprising a cyanine dye as light-absorbent compound in the information layer |
| US7041354B2 (en) | 2001-03-28 | 2006-05-09 | Bayer Aktiengesellschaft | Optical data carrier comprising a cyanine dye as light-absorbent compound in the information layer |
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