GB675227A - Improvements in or relating to cyanine dyes - Google Patents
Improvements in or relating to cyanine dyesInfo
- Publication number
- GB675227A GB675227A GB2699649A GB2699649A GB675227A GB 675227 A GB675227 A GB 675227A GB 2699649 A GB2699649 A GB 2699649A GB 2699649 A GB2699649 A GB 2699649A GB 675227 A GB675227 A GB 675227A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodide
- dimethyl
- methyl
- ethyl
- 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
- 239000000975 dye Substances 0.000 title abstract 3
- 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 abstract 3
- -1 acetamino Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- CQXUSMCVMOTSHH-UHFFFAOYSA-N 2-(2-ethylsulfanylethenyl)-1,3-benzoxazole Chemical compound C(C)SC=CC=1OC2=C(N1)C=CC=C2 CQXUSMCVMOTSHH-UHFFFAOYSA-N 0.000 abstract 1
- UTBVIMLZIRIFFR-UHFFFAOYSA-N 2-methylthio-1,3-benzothiazole Chemical compound C1=CC=C2SC(SC)=NC2=C1 UTBVIMLZIRIFFR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 241001061127 Thione Species 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000004832 aryl thioethers Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 238000004519 manufacturing process 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 125000000101 thioether group Chemical group 0.000 abstract 1
- 150000003568 thioethers Chemical class 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Cyanine dyes of the general formula <FORM:0675227/IV (c)/1> wherein R1 and R3 are alkyl, aralkyl, or aryl, R2 is alkyl or aralkyl, D1 and D2 are the residues of 5- or 6-membered heterocyclic nuclei, m and n are 0 or 1, x is 0 or 1, and X is an acid radical, are prepared by reacting a compound of the general formula <FORM:0675227/IV (c)/2> produced by the process of Specification 675,226, [Group IV (b)], with a compound of the general formula <FORM:0675227/IV (c)/3> wherein Y is an acid radical and Q is an alkyl-, aralkyl-, or aryl-thioether group or an amino or substituted amino (preferably acetamino or acetanilido) group. The reaction may be effected in the presence of a basic condensing agent, and the process may be modified by condensing a 2-acylmethylene heterocyclic base simultaneously with an alkyl-p-toluenesulphonate and a compound of the third general formula, which itself may be formed in situ by condensing the corresponding thione or thioether base with the alkyl-p-toluenesulphonate. Where Q is a thioether group and x is 1, the corresponding methyl derivative of the heterocyclic compound may be reacted with a trialkyl trithio-orthoformate in the presence of acetic anhydride, and the intermediate so obtained used without purification in the production of the dye. 3 : 31 - Dimethyl - 11 - methoxyoxathiadicarbocyanine iodide is prepared by refluxing together 2 - b - methyl : b - methoxyvinylbenzthiazole metho - p - toluenesulphonate, 2 - ethylthiovinylbenzoxazole metho - p - toluenesulphonate, ethanol, and triethylamine, and pouring into potassium iodide solution. 3 : 31-Dimethyl-9-methoxythiadicarbocyanine bromide and 1 : 31-dimethyl - 11 - methoxyindothiadicarbocyanine iodide are similarly prepared. 3 - Methyl - 31 - ethyl - 9 - methoxythiacarbocyanine iodide is prepared by fusing together 2-acetylmethylene - 3 - methyl - 2 : 3 - dihydrobenzthiazone and methyl p-toluenesulphonate, adding 2 - methylthiobenzthiazole ethiodide, ethanol, and triethylamine, and refluxing. 3 - Methyl - 31 - ethyl - 9 - ethoxythiacarbocyanine iodide, 3 : 31 - dimethyl - 9 - methoxythiacarbocyanine iodide, 3 : 31-dimethyl-9-ethoxythiacarbocyanine iodide, 3 : 31 - diethyl - 9 - ethoxythiacarbocyanine iodide, 3 : 31 - diethyl - 9 - methoxythiacarbocyanine iodide, 3 - ethyl - 31 - methyl - 9 - n-propoxythiacarbocyanine iodide, 3 : 31-dimethyl - 9 - n - propoxythiacarbocyanine iodide, 3 - methyl - 31 - ethyl - 9 - methoxy - 61 : 71 - benzthiacarbocyanine iodide, 3 : 11-dimethyl-9-methoxythiaquinocarbocyanine iodide, 1 : 31-dimethyl-9-methoxyindothiacarbocyanine perchlorate, 1 : 31-dimethyl - 9 - methoxyindoxacarbocyanine perchlorate, 3 - ethyl - 31 - methyl - 9 - methoxythiadicarbocyanine iodide, 1 - ethyl - 31 - methyl - 9 - methoxyindothiadicarbocyanine iodide, 1 : 31 - dimethyl - 11 - methoxyindothiadicarbocyaniniodide, 3 : 31 - diethyl - 9 - ethoxythiadicarbocyanine iodide, 3 : 31 - diethyl - 9 - methoxythiacarbocyanine iodide, 1 : 31 - dimethyl - 9 - methoxyindothiacarbocyanine perchlorate, 1 : 31 - dimethyl - 9 - methoxyindoxacarbocyanine perchlorate, and 3 : 31 - diethyl - 9 - b - phenylethoxythiacarbocyanine iodide are similarly prepared. According to the Provisional Specification, x may be 2. Specification 633,824 also is referred to.
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 |
|---|---|
| GB675227A true GB675227A (en) | 1952-07-09 |
Family
ID=10252453
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| GB2699649A Expired GB675227A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to cyanine dyes |
| 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 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 (2)
| 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 |
Country Status (2)
| Country | Link |
|---|---|
| GB (4) | GB672741A (en) |
| NL (2) | NL156707B (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 |
| CN109511264B (en) * | 2016-09-05 | 2021-06-08 | 株式会社艾迪科 | Polymethine compounds |
-
0
- NL NL75260D patent/NL75260C/xx active
- NL NL6616225.A patent/NL156707B/en unknown
-
1949
- 1949-10-20 GB GB2699249A patent/GB672741A/en not_active Expired
- 1949-10-20 GB GB2699649A patent/GB675227A/en not_active Expired
- 1949-10-20 GB GB2699349A patent/GB674003A/en not_active Expired
- 1949-10-20 GB GB2699449A patent/GB672291A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL156707B (en) | |
| GB672741A (en) | 1952-05-28 |
| NL75260C (en) | |
| GB674003A (en) | 1952-06-18 |
| GB672291A (en) | 1952-05-21 |
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