GB645967A - Improvements in or relating to cyanine dyestuffs - Google Patents
Improvements in or relating to cyanine dyestuffsInfo
- Publication number
- GB645967A GB645967A GB1364748A GB1364748A GB645967A GB 645967 A GB645967 A GB 645967A GB 1364748 A GB1364748 A GB 1364748A GB 1364748 A GB1364748 A GB 1364748A GB 645967 A GB645967 A GB 645967A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodide
- alkyl
- ethylbenzthiazole
- chlorobenzthiazole
- aralkyl
- 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 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 5
- IITIZHOBOIBGBW-UHFFFAOYSA-N 3-ethyl-2h-1,3-benzothiazole Chemical compound C1=CC=C2N(CC)CSC2=C1 IITIZHOBOIBGBW-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- -1 R5 is H Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- PQNQOHDLTYFBHE-UHFFFAOYSA-N 1-ethyl-2h-quinoline Chemical compound C1=CC=C2N(CC)CC=CC2=C1 PQNQOHDLTYFBHE-UHFFFAOYSA-N 0.000 abstract 1
- MFSHJZYOJOGIOO-UHFFFAOYSA-N 2-(5-chloro-2H-1,3-benzothiazol-3-yl)ethanol Chemical compound OCCN1CSC2=C1C=C(C=C2)Cl MFSHJZYOJOGIOO-UHFFFAOYSA-N 0.000 abstract 1
- HCTSMPZWZCJOKF-UHFFFAOYSA-N 5-chloro-3-ethyl-2h-1,3-benzothiazole Chemical compound C1=C(Cl)C=C2N(CC)CSC2=C1 HCTSMPZWZCJOKF-UHFFFAOYSA-N 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003367 polycyclic group Chemical group 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate 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
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Dicarbocyanine dyes are prepared by condensing a compound of the general formula <FORM:0645967/IV (c)/1> wherein R4 is alkyl, hydroxyalkyl, or aralkyl, R5 is H, alkyl, or aralkyl, n1 is 0 or 1, Y2 is an acid radicle, and D2 is the residue of a 5- or 6-membered heterocyclic ring, with a compound of one of the isomeric general formul <FORM:0645967/IV (c)/2> and <FORM:0645967/IV (c)/3> wherein X is alkyl or aryl, R1 is alkyl or aralkyl, R2 is alkyl, hydroxyalkyl, or aralkyl, R3 is H, alkyl, or aralkyl, n is 0 or 1, Y1 is an acid radicle, and D1 is the residue of a 5- or 6-membered heterocyclic nitrogen ring, the second reactant having been prepared by reacting an aldehyde of the formula X-CO-CH2-CHO with a mercaptan of the formula R1SH and reacting the product with a compound of the general formula <FORM:0645967/IV (c)/4> Where D1 and D2 are residues of polycyclic compounds, the carbocyclic rings may be substituted by one or more alkyl, aryl, amino, hydroxy, alkoxy, or methylene-dioxy groups or halogen atoms, and where R2 and R4 are hydroxyalkyl, the hydroxy groups may be acylated in the reaction. The condensation may be effected in presence of a base (e.g. pyridine, triethylamine, or sodium acetate). Bis - 2 - (3 - ethylbenzthiazole) - b - phenylpentamethinecyanine iodide is prepared by refluxing together 2-(b - or o -phenyl-o -ethylthiobutadienyl)-benzthiazole ethiodide, 2-methylbenzthiazole ethiodide, pyridine, and triethylamine. 2 - (1 - b - Acetoxyethylquinoline) - 21 - (1 - b - hydroxyethylquinoline) - b - or b 1 - phenylpenta-methinecyanine iodide, 2 - (3 - b - acetoxy - 5 - chlorobenzthiazole) - 21 - (3 - b - hydroxyethyl - 5 - chlorobenzthiazole) - b - or b 1 - phenylpenta-methinecyanine iodide, 2 - (3 - ethylbenzthiazole) - 21 - (3 - ethyl - 5 - chlorobenzthiazole) - b - or b 1 - methylpentamethinecyanine iodide, 2 - (3 - ethylbenzthiazole) - 21 - (1 - ethylquinoline) - b - or b 1\h - phenylpentamethinecyanine iodide, 2 - (3 - ethylbenzthiazole) - 21 - (3 - hydroxyethyl - 5 - chlorobenzthiazole) - b - or b 1 - phenylpentamethinecyanine iodide, 2 - (3 - b - acetoxyethyl - 5 - chlorobenzthiazole) - 21 - (3 - b - hydroxyethylbenzthiazole) - b - or b 1 - phenylpentamethinecyanine iodide, and 2-(3-ethylbenzthiazole)-21-(1 : 3 : 3-trimethylindolenine) - b - or b 1 - methylpentamethinecyanine iodide are similarly prepared. Specifications 645,965 and 645,966, [both in Group IV (b)], are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1364748A GB645967A (en) | 1948-05-20 | 1948-05-20 | Improvements in or relating to cyanine dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1364748A GB645967A (en) | 1948-05-20 | 1948-05-20 | Improvements in or relating to cyanine dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB645967A true GB645967A (en) | 1950-11-15 |
Family
ID=10026830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1364748A Expired GB645967A (en) | 1948-05-20 | 1948-05-20 | Improvements in or relating to cyanine dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB645967A (en) |
-
1948
- 1948-05-20 GB GB1364748A patent/GB645967A/en not_active Expired
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