GB835275A - Improvements in or relating to the production of cyanine dyes - Google Patents
Improvements in or relating to the production of cyanine dyesInfo
- Publication number
- GB835275A GB835275A GB3513056A GB3513056A GB835275A GB 835275 A GB835275 A GB 835275A GB 3513056 A GB3513056 A GB 3513056A GB 3513056 A GB3513056 A GB 3513056A GB 835275 A GB835275 A GB 835275A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- group
- ethyl
- benzthiazole
- nucleus
- 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 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 6
- -1 2-methyl-benzthiazole compound Chemical class 0.000 abstract 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- JYDHZOIDIWUHDB-UHFFFAOYSA-N 1-(4-phenylpiperidin-4-yl)ethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)C)CCNCC1 JYDHZOIDIWUHDB-UHFFFAOYSA-N 0.000 abstract 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 1
- YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 abstract 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 abstract 1
- NIFNXGHHDAXUGO-UHFFFAOYSA-N 5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC=NC2=CC=1C1=CC=CC=C1 NIFNXGHHDAXUGO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- FKYKJYSYSGEDCG-UHFFFAOYSA-N 6-methoxy-1,3-benzoxazole Chemical compound COC1=CC=C2N=COC2=C1 FKYKJYSYSGEDCG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- JLEKJZUYWFJPMB-UHFFFAOYSA-N ethyl 2-methoxyacetate Chemical compound CCOC(=O)COC JLEKJZUYWFJPMB-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 abstract 1
- 150000003568 thioethers 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
- C09B23/02—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
-
- 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
- C09B23/02—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)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Compounds of the general formula <FORM:0835275/IV (b)/1> wherein R1 is an alkyl, aryl or aralkyl group and X is hydrogen or one or more substituted halogen atoms, hydrocarbon, alkoxy or fused benz groups, are prepared by heating a 2-methyl-benzthiazole compound with a compound of the formula ROCH2COOR2 wherein R2 is a hydrocarbon group, in the presence of a strong base such as an alkali metal alkoxide. Examples are given of the reaction of 2-methyl-benzthiazole with ethyl ethoxyacetate, ethyl phenoxyacetate, or ethyl methoxyacetate in the presence of potassium ethoxide, and of the reaction of ethyl ethoxyacetate with 5 : 6-dimethoxy-, 5-chloro-, or 2 : 5-dimethyl-2-methylbenzthiazoles. According to the Provisional Specification, the reaction may be carried out with any heterocyclic nitrogen base having a reactive a -methyl group, such as the 2-methyl derivatives of benzoxazole, quinoline, indolenine, pyrroline and thiazoline.ALSO:Cyanine dyes of the general formula <FORM:0835275/IV(c)/1> wherein R1 is an alkyl, aryl or aralkyl group R3 is an alkyl, aralkyl or hydroxyalkyl group, X is hydrogen or one or more substituent halogen atoms or hydrocarbon, alkoxy or fused benz groups, D completes a 5- or 6-membered heterocyclic nucleus and n and m are 0 or 1, are prepared by reacting a benzthiazole having a 2-R1OCH2COCH- group with a compound of the formula <FORM:0835275/IV(c)/2> wherein Y is an anion and Q is a thioether, thioethervinyl or acetanilidovinyl group. Examples are given of the preparation of dyes wherein R1 is methyl, ethyl or phenyl, R3 is ethyl or methyl, X is H, 5-chloro, 5-methyl or 5 : 6-dimethoxy, and D completes a benzthiazole, benzoxazole, 5-chlorobenzthiazole, 5-phenylbenzoxazole, 6-methoxybenzoxazole, 5 : 6-dimethylbenzoxazole, thiazoline, 2 - quinoline, 3 : 3 - dimethylindolenine and 4 : 4 - dimethylpyrrolidine nucleus. According to the Provisional Specification, the right-hand nucleus of the dyes is not limited to benzthiazole but may be any 5- or 6-membered heterocyclic nitrogen nucleus similar to the nucleus completed by D.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3513056A GB835275A (en) | 1956-11-16 | 1956-11-16 | Improvements in or relating to the production of cyanine dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3513056A GB835275A (en) | 1956-11-16 | 1956-11-16 | Improvements in or relating to the production of cyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB835275A true GB835275A (en) | 1960-05-18 |
Family
ID=10374186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3513056A Expired GB835275A (en) | 1956-11-16 | 1956-11-16 | Improvements in or relating to the production of cyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB835275A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107033055A (en) * | 2015-12-28 | 2017-08-11 | 住友化学株式会社 | Light absorption compound and polymer composition, polymer film and cured film containing the compound |
-
1956
- 1956-11-16 GB GB3513056A patent/GB835275A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107033055A (en) * | 2015-12-28 | 2017-08-11 | 住友化学株式会社 | Light absorption compound and polymer composition, polymer film and cured film containing the compound |
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