GB385320A - Manufacture of cyanine dyes and the application thereof in photography - Google Patents
Manufacture of cyanine dyes and the application thereof in photographyInfo
- Publication number
- GB385320A GB385320A GB17051/31A GB1705131A GB385320A GB 385320 A GB385320 A GB 385320A GB 17051/31 A GB17051/31 A GB 17051/31A GB 1705131 A GB1705131 A GB 1705131A GB 385320 A GB385320 A GB 385320A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methiodide
- methylthiazoline
- condensed
- ethiodide
- dyes
- 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 10
- 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 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 9
- JUIQOABNSLTJSW-UHFFFAOYSA-N 2-Methyl-4,5-dihydro-1,3-thiazole Chemical compound CC1=NCCS1 JUIQOABNSLTJSW-UHFFFAOYSA-N 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 239000000839 emulsion Substances 0.000 abstract 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 6
- 150000003839 salts Chemical group 0.000 abstract 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 4
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 3
- ZGMNAIODRDOMEK-UHFFFAOYSA-N 1,1,1-trimethoxypropane Chemical compound CCC(OC)(OC)OC ZGMNAIODRDOMEK-UHFFFAOYSA-N 0.000 abstract 2
- PMYUGMDDIBOXQM-UHFFFAOYSA-M 1-ethylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2[N+](CC)=CC=CC2=C1 PMYUGMDDIBOXQM-UHFFFAOYSA-M 0.000 abstract 2
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 abstract 2
- LUYISICIYVKBTA-UHFFFAOYSA-N 6-methylquinoline Chemical compound N1=CC=CC2=CC(C)=CC=C21 LUYISICIYVKBTA-UHFFFAOYSA-N 0.000 abstract 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical compound C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 238000003287 bathing Methods 0.000 abstract 2
- 239000000298 carbocyanine Substances 0.000 abstract 2
- 229940072033 potash Drugs 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 235000015320 potassium carbonate Nutrition 0.000 abstract 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 2
- AGJZCWVTGOVGBS-UHFFFAOYSA-N 1,1'-diethyl-2,2'-cyanine Chemical compound C1=CC2=CC=CC=C2N(CC)\C1=C\C1=CC=C(C=CC=C2)C2=[N+]1CC AGJZCWVTGOVGBS-UHFFFAOYSA-N 0.000 abstract 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 abstract 1
- PNYRDWUKTXFTPN-UHFFFAOYSA-M 1-methylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2[N+](C)=CC=CC2=C1 PNYRDWUKTXFTPN-UHFFFAOYSA-M 0.000 abstract 1
- KPUBVYARPYJPPM-UHFFFAOYSA-N 2,5,5-trimethyl-4h-1,3-thiazole Chemical compound CC1=NCC(C)(C)S1 KPUBVYARPYJPPM-UHFFFAOYSA-N 0.000 abstract 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 abstract 1
- CGWAQZQRRWLHGO-UHFFFAOYSA-N 5,5-dimethyl-4h-1,3-thiazole Chemical compound CC1(C)CN=CS1 CGWAQZQRRWLHGO-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 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
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000002165 photosensitisation Effects 0.000 abstract 1
- 239000003504 photosensitizing agent Substances 0.000 abstract 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 230000035945 sensitivity Effects 0.000 abstract 1
- 230000001235 sensitizing effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 150000003549 thiazolines Chemical class 0.000 abstract 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 abstract 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
- G03C1/12—Methine and polymethine dyes
-
- 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
- C09B23/14—Styryl dyes
- C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US460548A US1942854A (en) | 1930-06-11 | 1930-06-11 | Photographic emulsion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB385320A true GB385320A (en) | 1932-12-12 |
Family
ID=23829156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17051/31A Expired GB385320A (en) | 1930-06-11 | 1931-06-11 | Manufacture of cyanine dyes and the application thereof in photography |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US1942854A (enrdf_load_stackoverflow) |
| BE (1) | BE380472A (enrdf_load_stackoverflow) |
| DE (1) | DE681505C (enrdf_load_stackoverflow) |
| FR (1) | FR718471A (enrdf_load_stackoverflow) |
| GB (1) | GB385320A (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435865A (en) * | 1944-10-17 | 1948-02-10 | Gen Aniline & Film Corp | Chain substituted cyanine dyes containing a carbonyl and thiocarbonyl group |
| US2552252A (en) * | 1948-03-26 | 1951-05-08 | Eastman Kodak Co | N, n'-diarylthiazolinocarbocyanine dyes |
| US2677683A (en) * | 1949-05-17 | 1954-05-04 | Gaspar | Cyclammonium quaternary salts and dyes produced thereof |
| US3125447A (en) * | 1960-11-25 | 1964-03-17 | Sensitized photoconductive compositions comprising zinc oxide | |
| US4097285A (en) * | 1977-02-17 | 1978-06-27 | Mitsubishi Paper Mills, Ltd. | Direct-positive photographic silver halide emulsion containing novel dye |
| DE69131075T2 (de) * | 1991-12-18 | 1999-08-12 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | Photographisches silberhalogenidmaterial |
-
0
- BE BE380472D patent/BE380472A/xx unknown
-
1930
- 1930-06-11 US US460548A patent/US1942854A/en not_active Expired - Lifetime
-
1931
- 1931-03-19 DE DEK119607D patent/DE681505C/de not_active Expired
- 1931-06-10 FR FR718471D patent/FR718471A/fr not_active Expired
- 1931-06-11 GB GB17051/31A patent/GB385320A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US1942854A (en) | 1934-01-09 |
| FR718471A (fr) | 1932-01-25 |
| DE681505C (de) | 1939-09-25 |
| BE380472A (enrdf_load_stackoverflow) |
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