GB672741A - Improvements in or relating to coumarin compounds, to methine dyes containing coumarin nuclei and to the preparation of such dyes - Google Patents
Improvements in or relating to coumarin compounds, to methine dyes containing coumarin nuclei and to the preparation of such dyesInfo
- Publication number
- GB672741A GB672741A GB2699249A GB2699249A GB672741A GB 672741 A GB672741 A GB 672741A GB 2699249 A GB2699249 A GB 2699249A GB 2699249 A GB2699249 A GB 2699249A GB 672741 A GB672741 A GB 672741A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyanocoumarin
- cyano
- general formula
- prepared
- methine
- 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 8
- 239000000975 dye Substances 0.000 title abstract 5
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title 2
- 229960000956 coumarin Drugs 0.000 title 1
- 235000001671 coumarin Nutrition 0.000 title 1
- 150000004775 coumarins Chemical class 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 12
- QKJALQPLNMEDAV-UHFFFAOYSA-N 2-oxochromene-3-carbonitrile Chemical compound C1=CC=CC2=C1OC(=O)C(C#N)=C2 QKJALQPLNMEDAV-UHFFFAOYSA-N 0.000 abstract 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- NVVMFSGDLVURFC-UHFFFAOYSA-N 3-methyl-3a,4-dihydro-2h-1,3-benzothiazole Chemical compound C1=CCC2N(C)CSC2=C1 NVVMFSGDLVURFC-UHFFFAOYSA-N 0.000 abstract 4
- FFBLBFMTKGSSPY-UHFFFAOYSA-N 4-methyl-2-oxochromene-3-carbonitrile Chemical compound C1=CC=CC2=C1OC(=O)C(C#N)=C2C FFBLBFMTKGSSPY-UHFFFAOYSA-N 0.000 abstract 4
- IJQYTHQDUDCJEQ-UHFFFAOYSA-N 7-hydroxy-2-oxochromene-3-carbonitrile Chemical compound C1=C(C#N)C(=O)OC2=CC(O)=CC=C21 IJQYTHQDUDCJEQ-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 3
- QYKOLWLKTJIVEX-UHFFFAOYSA-N 1-ethyl-3,4-dihydro-2h-quinoline Chemical compound C1=CC=C2N(CC)CCCC2=C1 QYKOLWLKTJIVEX-UHFFFAOYSA-N 0.000 abstract 2
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 abstract 2
- YURFGMWMMYWEKI-UHFFFAOYSA-N 3-ethyl-3a,4-dihydro-2H-1,3-benzothiazole Chemical compound C(C)N1CSC=2C1CC=CC2 YURFGMWMMYWEKI-UHFFFAOYSA-N 0.000 abstract 2
- GLGBPOSQDAZSIZ-UHFFFAOYSA-N 7-hydroxy-4-methyl-2-oxochromene-3-carbonitrile Chemical compound C1=C(O)C=CC2=C1OC(=O)C(C#N)=C2C GLGBPOSQDAZSIZ-UHFFFAOYSA-N 0.000 abstract 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-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
- DGYVIUKQSWPZCL-UHFFFAOYSA-N 3-methyl-1,3-thiazolidine Chemical compound CN1CCSC1 DGYVIUKQSWPZCL-UHFFFAOYSA-N 0.000 abstract 1
- CARFLRRKYDZASC-UHFFFAOYSA-N 3-methyl-3a,4-dihydro-2h-1,3-benzoxazole Chemical compound C1=CCC2N(C)COC2=C1 CARFLRRKYDZASC-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
- YVBSECQAHGIWNF-UHFFFAOYSA-N N-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2N(C)CCCC2=C1 YVBSECQAHGIWNF-UHFFFAOYSA-N 0.000 abstract 1
- -1 acetamino Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 125000005012 alkyl thioether group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 230000002087 whitening effect Effects 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
Abstract
Dye intermediates of the general formula <FORM:0672741/IV (b)/1> wherein D1 completes a benzene ring, are prepared by reacting a compound of the formula <FORM:0672741/IV (b)/2> with a lower alkyl ester of cyanacetic acid at high temperature in the presence of a basic compound. 3 - Cyano - 4 - methylcoumarin is prepared by heating together o-hydroxyacetophenone, ethyl cyanacetate, and triethylamine. 3-Cyano-4-methyl-7-hydroxycoumarin is similarly prepared.ALSO:Dyes of the general formula <FORM:0672741/IV (c)/1> wherein D1 completes a benzene ring, D2 completes a 5- or 6-membered heterocyclic ring system, and R2 is alkyl or aralkyl, are prepared by condensing a compound of the general formula <FORM:0672741/IV (c)/2> with a compound of the general formula <FORM:0672741/IV (c)/3> wherein X is an acid radical and R is alkyl. Methine - [2 - (3 - methyldihydrobenzthiazole)] - [4-(3-cyanocoumarin)] is prepared by refluxing together 3-cyano-4-methylcoumarin, 2-methylthiobenzthiazole methiodide, ethanol, and triethylamine. Methine - [2 - (3 - ethyldihydrobenzthiazole)] - [4 - (3 - cyanocoumarin)], methine - [2 - (1 - ethyldihydroquinoline)] - [4 - (3 - cyanocoumarin)], methine - [2 - (3 - methyltetrahydrothiazole)] - [4 - (3 - cyanocoumarin)], methine - [2 - (3 - methyl - 5 - methylthio - 1 : 3 : 4 - dihydrothiodiazole)] - [4 - (3 - cyanocoumarin)], methine - [2 - (3 - methyldihydrobenzthiazole)] - [4 - (3 - cyano - 7 - hydroxycoumarin)], and methine - [2 - (1 - methyldihydroquinoline)] - [4 - (3 - cyano - 7 - hydroxycoumarin)] are similarly prepared. Dyes of the general formula <FORM:0672741/IV (c)/4> where D1, D2, and R2 are as before, are prepared by condensing an intermediate of the second general formula above with an intermediate of the general formula <FORM:0672741/IV (c)/5> wherein X is an acid radical and Q an alkylthioether, amino, or substituted amino (e.g. acetamino or acetanilido) group. Trimethine - [2 - (1 : 3 : 3 - trimethyldihydroindole)] - [4 - (3 - cyanocoumarin)] is prepared by refluxing together 3-cyano-4-methylcoumarin, 2 - (b - methylthiovinyl) - 3 : 3 - dimethylindolenine methiodide, ethanol, and triethylamine. Trimethine - [2 - (3 - methyldihydrobenzoxazole)] - [4 - (3 - cyanocoumarin)], trimethine - [2 - (3 - methyldihydrobenzthiazole)] - [4 - (3 - cyanocoumarin)], trimethine - [4 - (1 - ethyldihydroquinoline)] - [4 - (3 - cyanocoumarin)], trimethine - [2 - (1 : 3 : 3 - trimethyldihydroindole)] - [4 - (3 - cyano - 7 - hydroxycoumarin)], and trimethine - [2 - (3 - methyldihydrobenzthiazole)] - [4 - (3 - cyano - 7 - hydroxycoumarin)] are similarly prepared. Dyes of the general formula <FORM:0672741/IV (c)/6> wherein R3 is an alkyl group, are prepared by condensing an intermediate of the second general formula with a compound of the general formula <FORM:0672741/IV (c)/7> wherein X is an acid radical and R is an alkyl group. b - Methylthiotrimethine - [2 - (3 - ethyldihydrobenzthiazole)] - [4 - (3 - cyanocoumarin)] is prepared by refluxing together 3-cyano-4-methylcoumarin, 2-b -di-(methylthio)-vinylbenzthiazole ethiodide, ethanol, and triethylamine. 3-Cyano-4-methyl-7-hydroxycoumarin has a strong bluish fluorescence and can be applied to textile fabrics to impart a whitening effect or to render the colour more brilliant.
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 |
|---|---|
| GB672741A true GB672741A (en) | 1952-05-28 |
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 |
| GB2699449A Expired GB672291A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to photographic sensitising dyes |
| GB2699349A Expired GB674003A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to methine dyestuffs and photographic emulsions containing the same |
| GB2699649A Expired GB675227A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to cyanine 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 |
| GB2699349A Expired GB674003A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to methine dyestuffs and photographic emulsions containing the same |
| GB2699649A Expired GB675227A (en) | 1949-10-20 | 1949-10-20 | Improvements in or relating to cyanine dyes |
Country Status (2)
| Country | Link |
|---|---|
| GB (4) | GB672741A (en) |
| NL (2) | NL75260C (en) |
Cited By (2)
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7000329B2 (en) * | 2016-09-05 | 2022-01-19 | 株式会社Adeka | Polymethin compound |
-
0
- NL NL6616225.A patent/NL156707B/en unknown
- NL NL75260D patent/NL75260C/xx active
-
1949
- 1949-10-20 GB GB2699249A patent/GB672741A/en not_active Expired
- 1949-10-20 GB GB2699449A patent/GB672291A/en not_active Expired
- 1949-10-20 GB GB2699349A patent/GB674003A/en not_active Expired
- 1949-10-20 GB GB2699649A patent/GB675227A/en not_active Expired
Cited By (2)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL75260C (en) | |
| GB674003A (en) | 1952-06-18 |
| NL156707B (en) | |
| GB672291A (en) | 1952-05-21 |
| GB675227A (en) | 1952-07-09 |
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