GB642517A - Improvements in or relating to polymethine dyestuffs - Google Patents
Improvements in or relating to polymethine dyestuffsInfo
- Publication number
- GB642517A GB642517A GB2572848A GB2572848A GB642517A GB 642517 A GB642517 A GB 642517A GB 2572848 A GB2572848 A GB 2572848A GB 2572848 A GB2572848 A GB 2572848A GB 642517 A GB642517 A GB 642517A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- ethylthio
- cyano
- hexadienoate
- methyl
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- -1 heterocyclic thioether compound Chemical class 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- LLSSBOPMPRCWRG-UHFFFAOYSA-N ethyl 2-cyano-3-ethylsulfanylbut-2-enoate Chemical compound CCOC(=O)C(C#N)=C(C)SCC LLSSBOPMPRCWRG-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000101 thioether group Chemical group 0.000 abstract 2
- JUIQOABNSLTJSW-UHFFFAOYSA-N 2-Methyl-4,5-dihydro-1,3-thiazole Chemical compound CC1=NCCS1 JUIQOABNSLTJSW-UHFFFAOYSA-N 0.000 abstract 1
- BENTUJDVVCBSRS-UHFFFAOYSA-N 2-methyl-4,5-dihydro-1,3-selenazole Chemical compound CC1=NCC[Se]1 BENTUJDVVCBSRS-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
- BOYVBHABOSBRJQ-UHFFFAOYSA-N 6-ethoxy-1,5,2,3,4-dioxatrithiane Chemical compound C1(OCC)OSSSO1 BOYVBHABOSBRJQ-UHFFFAOYSA-N 0.000 abstract 1
- KYLIZBIRMBGUOP-UHFFFAOYSA-N Anetholtrithion Chemical group C1=CC(OC)=CC=C1C1=CC(=S)SS1 KYLIZBIRMBGUOP-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical group 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
- C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Methine dyes are prepared by reacting a compound of the general formula <FORM:0642517/IV (c)/1> or a stereoisomeric form thereof, wherein R1 is alkyl (including hexyl, octyl, and dodecyl), R3 is alkyl or aralkyl, and R4 is H or alkyl, with a compound of the general formula <FORM:0642517/IV (c)/2> wherein Q is a thioether group SR6 (R6 being alkyl) or a substituted or unsubstituted amino group, R5 is alkyl or aralkyl, X is an acid radical, n is 0 or 1, and D is the residue of a 5- or 6-membered heterocyclic nucleus, which may have substituted or unsubstituted carbocyclic rings fused thereto. Where Q is a thioether group, the heterocyclic thioether compound need not be isolated, and the quaternary salt of the heterocyclic compound containing a reactive methyl group in a - or g -position to the quaternary N atom may be reacted with a trialkyl trithio orthoformate in presence of acetic anhydride and the product reacted directly with the compound of the first general formula. Ethyl 6 - (3 - ethyl - 2 : 3 - dihydrobenzthiazolylidene - 2) - 3 - ethylthio - 2 - cyano-2 : 4- hexadienoate is prepared by boiling together 2 - o - acetanilidovinylbenzthiazole ethiodide and ethyl 2 - cyano - 3 - ethylthio - 2-butenoate in pyridine. Ethyl 6-(3-methyltetrahydrothiazolylidene - 2) - 3 - ethylthio - 2 - cyano-2 : 4 - hexadienoate is prepared by fusing together 2-methylthiazoline and methyl p-toluenesulphonate, adding ethyl trithio orthoformate and boiling gently in acetic anhydride, distilling off the acetic anhydride in vacuo and dissolving the remaining oil in ethyl alcohol, adding ethyl 2 - cyano - 3 - ethylthio - 2-butenoate and triethylamine, and refluxing. Ethyl 6 - (3 - methyl - 2 : 3 - dihydrobenzoxazolylidene - 2) - 3 - ethylthio - 2 - cyano - 2 : 4 - hexadienoate and the corresponding methyl ester, ethyl 6 - (3 - methyl - 2 : 3 - dihydrobenzthiazolylidene - 2) - 3 - methylthio - 2 - cyano - 2 : 4-hexadienoate, and the corresponding 3-ethylthio, 3 - isopropylthio, 3 - n - butylthio - and 3-benzylthio derivatives, the corresponding 3-ethyl derivatives, and the corresponding methyl 3-methyl, 3-methylthio and 3-ethylthio derivatives, ethyl 6 - (3 - ethyltetrahydrothiazolylidene - 2) - 3 - ethylthio - 2 - cyano - 2 : 4-hexadienoate, ethyl 6 - (3 - ethyl - 2 : 3 - dihydro-4 : 5 - benzbenzthiazolylidene - 2) - 3 - ethylthio-2 - cyano - 2 : 4 - hexadienoate and the corresponding 3-methyl, 3-methylthio and 3-ethylthio derivatives, ethyl 6-(3-methyl-2 : 3-dihydro-5-phenylbenzoxazolylidene - 2) - 3 - ethylthio - 2-cyano-2 : 4-hexadienoate and the corresponding 3-ethyl and 3-methylthio derivatives, ethyl 6-1 - ethyl - 1 : 2 - dihydroquinolylidene - 2) - 3-ethylthio - 2 - cyano - 2 : 4 - hexadienoate, ethyl 6 - (1 : 3 : 3 - trimethyl - 1 : 2 - dihydrindolylidene - 2) - 3 - ethylthio - 2 - cyano - 2 : 5 - hexadienoate, ethyl 6 - (2 - methyl - 2 : 3 - dihydro-6 : 7 - benzbenzthiazolylidene - 2) - 3 - ethylthio-2 - cyano - 2 : 4 - hexadienoate, ethyl 6 - (3-ethyl - 2 : 2 - dihydro - 5 : 6 - dioxymethylene benzthiazolylidene - 2) - 3 - ethylthio - - 2 cyano-2 : 4 - hexadienoate, ethyl 6 - (3 - methyl - 2 : 3-dihydro - 5 : 6 - dimethylbenzoxazolylidene - 2)-3 - methylthio - 2 - cyano - 2 : 4 - hexadienoate. and ethyl 6 - (1 - methyl - 1 : 2 - dihydroquinolylidene - 4) - 3 - methylthio - 2 - cyano - 2 : 4-hexadienoate are similarly prepared. Similar dyes may be prepared from 2-methyl-selenazoline, -oxazoline, -benzselenazole, -pyrimidine, and -quinazoline. Specification 642,514, [Group IV (b)], is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2572848A GB642517A (en) | 1948-10-02 | 1948-10-02 | Improvements in or relating to polymethine dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2572848A GB642517A (en) | 1948-10-02 | 1948-10-02 | Improvements in or relating to polymethine dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB642517A true GB642517A (en) | 1950-09-06 |
Family
ID=10232324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2572848A Expired GB642517A (en) | 1948-10-02 | 1948-10-02 | Improvements in or relating to polymethine dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB642517A (en) |
-
1948
- 1948-10-02 GB GB2572848A patent/GB642517A/en not_active Expired
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