GB633873A - Improvements in the manufacture of methin dyes containing an isoquinoline nucleus and in photographic emulsions containing them - Google Patents
Improvements in the manufacture of methin dyes containing an isoquinoline nucleus and in photographic emulsions containing themInfo
- Publication number
- GB633873A GB633873A GB10482/47A GB1048247A GB633873A GB 633873 A GB633873 A GB 633873A GB 10482/47 A GB10482/47 A GB 10482/47A GB 1048247 A GB1048247 A GB 1048247A GB 633873 A GB633873 A GB 633873A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodide
- ethyl
- methyl
- perchlorate
- alkyl
- 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 2
- 239000000839 emulsion Substances 0.000 title 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 20
- PBYMYAJONQZORL-UHFFFAOYSA-N 2-methylisoquinoline Natural products C1=CC=C2C(C)=NC=CC2=C1 PBYMYAJONQZORL-UHFFFAOYSA-N 0.000 abstract 11
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 238000010992 reflux Methods 0.000 abstract 5
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 5
- -1 2 - ethyl - 1 - isoquinolylidene Chemical group 0.000 abstract 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 abstract 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 150000003839 salts Chemical group 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 abstract 2
- DLHWKJDYXPNWAI-UHFFFAOYSA-N 2,2,2-trichloro-1-ethoxyethanol Chemical compound CCOC(O)C(Cl)(Cl)Cl DLHWKJDYXPNWAI-UHFFFAOYSA-N 0.000 abstract 1
- UBQYLZLUIAYQHL-UHFFFAOYSA-N 2-[5-[2-(2-ethylisoquinolin-1-ylidene)ethylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C(=O)(O)CN1C(SC(C1=O)=CC=C1N(C=CC2=CC=CC=C12)CC)=S UBQYLZLUIAYQHL-UHFFFAOYSA-N 0.000 abstract 1
- IEXYLQOPBXUDSK-UHFFFAOYSA-N 2-methylisoquinoline-1-thione Chemical compound C1=CC=C2C(=S)N(C)C=CC2=C1 IEXYLQOPBXUDSK-UHFFFAOYSA-N 0.000 abstract 1
- VFCZOISUYOEWFI-UHFFFAOYSA-N 3-ethyl-5-[2-(2-ethylisoquinolin-1-ylidene)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C(C)N1C(SC(C1=O)=CC=C1N(C=CC2=CC=CC=C12)CC)=S VFCZOISUYOEWFI-UHFFFAOYSA-N 0.000 abstract 1
- RDNJBRIEZBQNTR-UHFFFAOYSA-N 3-ethyl-5-[2-(2-methylisoquinolin-1-ylidene)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C(C)N1C(SC(C1=O)=CC=C1N(C=CC2=CC=CC=C12)C)=S RDNJBRIEZBQNTR-UHFFFAOYSA-N 0.000 abstract 1
- JKSQWGKNCXXZKT-UHFFFAOYSA-N 3-methyl-4-[2-(2-methylisoquinolin-1-ylidene)ethylidene]-1-(5-oxo-4H-pyrazol-1-yl)cyclohexa-2,5-diene-1-sulfonic acid Chemical compound CN1C(C2=CC=CC=C2C=C1)=CC=C1C(=CC(C=C1)(S(=O)(=O)O)N1N=CCC1=O)C JKSQWGKNCXXZKT-UHFFFAOYSA-N 0.000 abstract 1
- LMSUDJGROGIBAO-UHFFFAOYSA-N 3-phenyl-5-[2-(2-propylisoquinolin-1-ylidene)ethylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1(=CC=CC=C1)N1C(SC(C1=O)=CC=C1N(C=CC2=CC=CC=C12)CCC)=S LMSUDJGROGIBAO-UHFFFAOYSA-N 0.000 abstract 1
- BDPACSRDBXJXPQ-UHFFFAOYSA-N 4-[2-(2-ethylisoquinolin-1-ylidene)ethylidene]-5-methyl-2-phenylpyrazol-3-one Chemical compound C(C)N1C(C2=CC=CC=C2C=C1)=CC=C1C(=NN(C1=O)C1=CC=CC=C1)C BDPACSRDBXJXPQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 229950005228 bromoform Drugs 0.000 abstract 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 abstract 1
- 229960002327 chloral hydrate Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002537 isoquinolines Chemical class 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 abstract 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 abstract 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 abstract 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/83—Organic dyestuffs therefor
- G03C1/832—Methine or polymethine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
- Quinoline Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US663619A US2518737A (en) | 1946-04-19 | 1946-04-19 | Methine dyes containing an isoquinoline nucleus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB633873A true GB633873A (en) | 1949-12-30 |
Family
ID=24662598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10482/47A Expired GB633873A (en) | 1946-04-19 | 1947-04-19 | Improvements in the manufacture of methin dyes containing an isoquinoline nucleus and in photographic emulsions containing them |
Country Status (4)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496730A (en) * | 1982-09-20 | 1985-01-29 | Eastman Kodak Company | Phosphorous diketonate electron accepting ring compounds as sensitizers for electron donating photoconductive compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102408373B (zh) * | 2011-10-26 | 2014-04-16 | 上海煦旻化工科技发展有限公司 | 1-甲基异喹啉的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2071899A (en) * | 1930-05-31 | 1937-02-23 | Ici Ltd | Sensitized photographic film, plate, and emulsion |
| DE576532C (de) * | 1930-11-28 | 1933-05-17 | C H Boehringer Sohn A G | Verfahren zur Darstellung von Isochinolinabkoemmlingen |
| GB413300A (en) * | 1933-01-09 | 1934-07-09 | Kodak Ltd | Improvements in the manufacture of dyestuffs and intermediates therefor |
| US2189599A (en) * | 1933-01-16 | 1940-02-06 | Eastman Kodak Co | Process of preparing cyanine dyes with strong organic bases |
| US2202827A (en) * | 1934-10-25 | 1940-06-04 | Eastman Kodak Co | Process of preparing cyanine dyes from substituted mercapto derivatives |
| GB477983A (en) * | 1936-04-06 | 1938-01-06 | Mark Barent | Improvements in or relating to the production of photographic sensitising compounds |
-
0
- BE BE473032D patent/BE473032A/xx unknown
-
1946
- 1946-04-19 US US663619A patent/US2518737A/en not_active Expired - Lifetime
-
1947
- 1947-04-19 GB GB10482/47A patent/GB633873A/en not_active Expired
- 1947-04-19 FR FR948101D patent/FR948101A/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496730A (en) * | 1982-09-20 | 1985-01-29 | Eastman Kodak Company | Phosphorous diketonate electron accepting ring compounds as sensitizers for electron donating photoconductive compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE473032A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| FR948101A (fr) | 1949-07-22 |
| US2518737A (en) | 1950-08-15 |
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