GB674003A - Improvements in or relating to methine dyestuffs and photographic emulsions containing the same - Google Patents
Improvements in or relating to methine dyestuffs and photographic emulsions containing the sameInfo
- Publication number
- GB674003A GB674003A GB2699349A GB2699349A GB674003A GB 674003 A GB674003 A GB 674003A GB 2699349 A GB2699349 A GB 2699349A GB 2699349 A GB2699349 A GB 2699349A GB 674003 A GB674003 A GB 674003A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- ethyl
- cyano
- hexadienoate
- ethoxy
- 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
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title abstract 2
- 239000000839 emulsion Substances 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- -1 2 - dihydroindolylidene Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000000975 dye Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- HBBOGXAEKAVLGW-UHFFFAOYSA-N bis(ethylsulfanyl)methylsulfanylethane Chemical compound CCSC(SCC)SCC HBBOGXAEKAVLGW-UHFFFAOYSA-N 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005012 alkyl thioether group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- YKXFOGAYPIPTKF-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxybut-2-enoate Chemical compound CCOC(C)=C(C#N)C(=O)OCC YKXFOGAYPIPTKF-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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 abstract 1
- 238000005406 washing Methods 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
-
- 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
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/0025—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being bound through an oxygen atom
-
- 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
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
-
- 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
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Dyes of the general formula <FORM:0674003/IV (c)/1> wherein R1 is alkyl, R2 and R3 are alkyl o aralkyl, n is 0 or 1, and D is the residue of a 5- or 6-membered heterocyclic ring system of the type used in cyanine dyes, are prepared by reacting a compound of the general formula <FORM:0674003/IV (c)/2> with a compound of the general formula <FORM:0674003/IV (c)/3> wherein X is an acid radicle and Q is an alkyl thioether, amino, or substituted amino group. The condensation may be effected in the presence of a basic condensing agent. The methyl derivative corresponding to the compound of the last-mentioned general formula may be reacted with triethyl trithio-orthoformate and the condensation with the compound of the second general formula effected without isolating the reaction product. Ethyl 6 - (3 - methyl - 2 : 3 - dihydrobenzthiazolylidene - 2) - 3 - ethoxy - 2 - cyano - 2 : 4 - hexadienoate is prepared by fusing 2-methylbenzthiazole with methyl p-toluenesulphonate, adding triethyl trithio-orthoformate and acetic anhydride and refluxing, distilling off the acetic anhydride in vacuo, washing the residual oil with ether and dissolving in ethyl alcohol, adding ethyl 2-cyano-3-ethoxy-2-butenoate and refluxing. Ethyl and methyl 6-(3-methyl-2 : 3-dihydrobenzthiazolylidene - 2) - 3 - methoxy - 2 - cyano - 2 : 4 - hexadienoate, methyl 6 - (3 - methyl-2 : 3 - dihydrobenzthiazolelidene - 2) - 3 - ethoxy - 2-cyano-2 : 4-hexadienoate, ethyl 6-(1 : 3 : 3-trimethyl - 1 : 2 - dihydroindolylidene - 2) - 3 - ethoxy-2 - cyano - 2 : 4 - hexadienoate, ethyl 6 - (1 : 3 : 3 - trimethyl - 1 : 2 - dihydroindolylidene - 2) - 3 - methoxy - cyano - 2 : 4 - hexadienoate, ethyl 6 - (3-ethyl - 2 : 3 - dihydrobenzthiazolylidene - 2) - 3 - ethoxy - 2 - cyano - 2 : 4 - hexadienoate, ethyl 6 - (3 - ethyl - 2 : 3 - dihydrobenzthiazolylidene - 2) - 3-methoxy - 2 - cyano - 2 : 4 - hexadienoate, ethyl 6 - (3 - methyl - 2 : 3 - dihydrobenzoxazolylidene - 2) - 3 - ethoxy - 2 - cyano - 2 : 4 - hexadienoate, methyl 6 - (3 - methyl - 2 : 3 - dihydrobenzoxazolylidene - 2) - 3 - methoxy - 2 - cyano - 2 : 4 - hexadienoate, ethyl 6 - (I - methyl - 1 : 4 - dihydroquinolylidene - 4) - 3 - ethoxy - 2 - cyano - 2 : 4 - hexadienoate, methyl - 6 - (1 - methyl - 1 : 4 - dihydroquinolylidene - 4) - 3 - methoxy - 2 - cyano - 2 : 4 - hexadienoate, ethyl 6-(3-ethyl-2 : 3-dihydro-4 : 5-benzbenzthiazolylidene - 2) - 3 - ethoxy - 2 - cyano - 2 : 4 - hexadienoate, and methyl 6-(3-ethyl-2 : 3-dihydro - 4 : 5 - benzbenzthiazolylidene - 2) - 3 - methoxy - 2 - cyano - 2 : 4 - hexadienoate are similarly prepared. According to the Provisional Specification, the methyl group in the first reactant may be replaced by a group -CH2R4, wherein R4 is an alkyl, aralkyl, or aryl group, giving rise to dyes in which the central methine group of the pentamethine chain is substituted by the group R4, and the group R3 may be an aryl group.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2699449A GB672291A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to photographic sensitising dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB674003A true GB674003A (en) | 1952-06-18 |
Family
ID=10252453
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2699349A Expired GB674003A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to methine dyestuffs and photographic emulsions containing the same |
| GB2699449A Expired GB672291A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to photographic sensitising dyes |
| GB2699649A Expired GB675227A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to cyanine dyes |
| GB2699249A Expired GB672741A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to coumarin compounds, to methine dyes containing coumarin nuclei and to the preparation of such dyes |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2699449A Expired GB672291A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to photographic sensitising dyes |
| GB2699649A Expired GB675227A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to cyanine dyes |
| GB2699249A Expired GB672741A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to coumarin compounds, to methine dyes containing coumarin nuclei and to the preparation of such dyes |
Country Status (2)
| Country | Link |
|---|---|
| GB (4) | GB674003A (en) |
| NL (2) | NL75260C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3146101A (en) * | 1962-05-31 | 1964-08-25 | Minnesota Mining & Mfg | Sensitization of photoconductive copysheets |
| US4299894A (en) * | 1980-06-23 | 1981-11-10 | Eastman Kodak Company | Electrically photosensitive materials and elements for photoelectrophoretic imaging processes |
| KR102507765B1 (en) * | 2016-09-05 | 2023-03-08 | 가부시키가이샤 아데카 | polymethine compounds |
-
0
- NL NL6616225.A patent/NL156707B/en unknown
- NL NL75260D patent/NL75260C/xx active
-
1949
- 1949-10-20 GB GB2699349A patent/GB674003A/en not_active Expired
- 1949-10-20 GB GB2699449A patent/GB672291A/en not_active Expired
- 1949-10-20 GB GB2699649A patent/GB675227A/en not_active Expired
- 1949-10-20 GB GB2699249A patent/GB672741A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL75260C (en) | |
| GB672741A (en) | 1952-05-28 |
| GB675227A (en) | 1952-07-09 |
| GB672291A (en) | 1952-05-21 |
| NL156707B (en) |
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