GB604217A - Improvements in or relating to cyanine dyestuffs and to photographic silver halide emulsions sensitised therewith - Google Patents
Improvements in or relating to cyanine dyestuffs and to photographic silver halide emulsions sensitised therewithInfo
- Publication number
- GB604217A GB604217A GB1687645A GB1687645A GB604217A GB 604217 A GB604217 A GB 604217A GB 1687645 A GB1687645 A GB 1687645A GB 1687645 A GB1687645 A GB 1687645A GB 604217 A GB604217 A GB 604217A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexenone
- ethylthio
- methyl
- refluxing
- toluenesulphonate
- 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
- -1 silver halide Chemical class 0.000 title abstract 2
- 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
- 239000000839 emulsion Substances 0.000 title 1
- 229910052709 silver Inorganic materials 0.000 title 1
- 239000004332 silver Substances 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 6
- 238000010992 reflux Methods 0.000 abstract 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 3
- RSHVGYCVPWDHQM-UHFFFAOYSA-N C[S+]1C(C=CC=C2Cl)=C2N=C1 Chemical compound C[S+]1C(C=CC=C2Cl)=C2N=C1 RSHVGYCVPWDHQM-UHFFFAOYSA-N 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 abstract 2
- VGGUVGVAVAAODK-ZROIWOOFSA-N (5z)-2-amino-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1\C=C1/SC(=N)NC1=O VGGUVGVAVAAODK-ZROIWOOFSA-N 0.000 abstract 1
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical compound C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 abstract 1
- SNHUPGJQDQJZKL-UHFFFAOYSA-N 1-methyl-1lambda4,3-benzoselenazole Chemical compound C[SeH]1C=NC2=C1C=CC=C2 SNHUPGJQDQJZKL-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
- JKLZCQWVERBDEZ-UHFFFAOYSA-N 3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound CN1C(=O)CSC1=S JKLZCQWVERBDEZ-UHFFFAOYSA-N 0.000 abstract 1
- MVVFUAACPKXXKJ-UHFFFAOYSA-N 4,5-dihydro-1,3-selenazole Chemical compound C1CN=C[Se]1 MVVFUAACPKXXKJ-UHFFFAOYSA-N 0.000 abstract 1
- FUJKCTSXPWXOHR-UHFFFAOYSA-N 4-phenylcyclohexane-1,2-dione Chemical compound C1C(=O)C(=O)CCC1C1=CC=CC=C1 FUJKCTSXPWXOHR-UHFFFAOYSA-N 0.000 abstract 1
- SJLJHVITDDTVMW-UHFFFAOYSA-N C[S+]1C2=CC=CC=C2N=C1 Chemical compound C[S+]1C2=CC=CC=C2N=C1 SJLJHVITDDTVMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract 1
- 229940091173 hydantoin Drugs 0.000 abstract 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 abstract 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003367 polycyclic group Chemical group 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 abstract 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-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
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Symmetrical cyanine dyes are prepared by condensing a cyclohexane 1 : 3-dione, a D 2 : 3-(3-alkylthio)-cyclohexenone (1) or a D 2 : 3-(3-aralkylthio)-cyclohexenone (1) with an alkyl or aralkyl quaternary salt of a thiazole or selenazole or polycyclic homologue, a thiazoline selenazoline, diazine, or diazole or with rhodanine or a N-hydrocarbon substituted derivative, or with an oxindole, pyrazole-5-one, hydantoin, thiohydantoin, pseudohydantoin, or pseudothiohydantoin by heating together in presence of a base, preferably in presence of a solvent for the reactants. The D 2 : 3-(3-alkylthio)-cyclohexenone (1) may be one of those of Specification 595,783. In examples, dyes are prepared (1) by fusing together D 2 : 3-(3-ethylthio-5 : 5-dimethyl)-cyclohexenone (1), 1-methylbenzthiazole, and methyl p-toluenesulphonate, and pyridine and refluxing, adding triethylamine and further refluxing, and pouring into aqueous KI solution; (2) as in (1), using ethyl p-toluenesulphonate; (3) as in (2), using 1-methyl-4-chlorobenzthiazole; (4) as in (2), using 1-methylbenzselenazole; (5) by fusing together 5 : 5-dimethylcyclohexane dione (1 : 3), 1 : 4-dimethylbenzthiazole and ethyl p-toluenesulphonate, adding pyridine and triethylamine and refluxing, and pouring into aqueous KI solution; (6) as in (2), using D 2 : 3 - (3 - ethylthio - 5 - methyl) - cyclohexenone (1); (7) as in (2), using D 2 : 3-(3-ethylthio-5-phenyl)-cyclohexenone (1); (8) as in (5), using 5-phenylcyclohexane dione (1 : 3); (9) by fusing together D 2 : 3-(3-ethylthio-5 : 5-dimethyl)-cyclohexenone (1) and 1-phenyl-3-methyl-5-pyrazolone, adding pyridine and refluxing, adding triethylamine and refluxing, and acidifying; (10) as in (9), using N-methylrhodanine; (11) as in (6), using 1-methyl-4-chlorobenzthiazole; and (12) as in (2) using D 2 : 3-(3-ethylthio)-cyclohexenone (1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1687645A GB604217A (en) | 1945-07-03 | 1945-07-03 | Improvements in or relating to cyanine dyestuffs and to photographic silver halide emulsions sensitised therewith |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1687645A GB604217A (en) | 1945-07-03 | 1945-07-03 | Improvements in or relating to cyanine dyestuffs and to photographic silver halide emulsions sensitised therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB604217A true GB604217A (en) | 1948-06-30 |
Family
ID=10085264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1687645A Expired GB604217A (en) | 1945-07-03 | 1945-07-03 | Improvements in or relating to cyanine dyestuffs and to photographic silver halide emulsions sensitised therewith |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB604217A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5296343A (en) * | 1990-10-08 | 1994-03-22 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and full color recording material containing the same |
| US5518876A (en) * | 1992-12-16 | 1996-05-21 | Eastman Kodak Company | Red sensitizers for high silver chloride emulsions |
-
1945
- 1945-07-03 GB GB1687645A patent/GB604217A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5296343A (en) * | 1990-10-08 | 1994-03-22 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and full color recording material containing the same |
| US5518876A (en) * | 1992-12-16 | 1996-05-21 | Eastman Kodak Company | Red sensitizers for high silver chloride emulsions |
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