GB642515A - Improvements in or relating to dyestuffs - Google Patents
Improvements in or relating to dyestuffsInfo
- Publication number
- GB642515A GB642515A GB2572648A GB2572648A GB642515A GB 642515 A GB642515 A GB 642515A GB 2572648 A GB2572648 A GB 2572648A GB 2572648 A GB2572648 A GB 2572648A GB 642515 A GB642515 A GB 642515A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- alkyl
- cyano
- butenoate
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- -1 6-membered heterocyclic nitrogen compound Chemical class 0.000 abstract 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 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
- 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 1
- WBFIDNBLYWSNJB-UHFFFAOYSA-N ethyl 2-cyano-3-ethylsulfanylpent-2-enoate Chemical compound C(#N)C(C(=O)OCC)=C(CC)SCC WBFIDNBLYWSNJB-UHFFFAOYSA-N 0.000 abstract 1
- YHBAOWXDJHAQJQ-UHFFFAOYSA-N ethyl 2-cyano-3-methylsulfanylbut-2-enoate Chemical compound CCOC(=O)C(C#N)=C(C)SC YHBAOWXDJHAQJQ-UHFFFAOYSA-N 0.000 abstract 1
- NWOKVFOTWMZMHL-UHFFFAOYSA-N ethyl 2-cyanoacetoacetate Chemical compound CCOC(=O)C(C#N)C(C)=O NWOKVFOTWMZMHL-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910017464 nitrogen compound Inorganic materials 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
- 238000010992 reflux Methods 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 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
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Ethyl 2 - cyano - 3 - methylthio - 2 - butenoate is prepared by adding ethyl a -cyanoacetoacetate to a dry ether solution of methyl mercaptan, cooling, and adding anhydrous zinc chloride. Ethyl 2-cyano-3-ethylthio-2-pentenoate is similarly prepared. Specification 642,514 is referred to.ALSO:Methine dyes are prepared by condensing a compound of the general formula <FORM:0642515/IV (c)/1> or a stereoisomer thereof, where R1 and R2 are alkyl (including hexyl, octyl, and dodecyl) groups and R3 is an alkyl or aralkyl group, with an alkyl or aralkyl quaternary salt of a 5- or 6-membered heterocyclic nitrogen compound which may have substituted or unsubstituted carbocyclic rings fused thereto) having a reactive -CH2R4 group, wherein R4 is H or alkyl, in a - or g -position to the quaternary nitrogen atom. Ethyl 4-(3-ethyl-2 : 3-dihydrobenzthiazolylidene - 2) - 3 - methyl - 2 - cyano - 2 - butenoate is prepared by refluxing together ethyl 2 - cyano - 3 - ethylthio - 2 - butenoate, 2 - methylbenzthiazole ethiodide, and triethylamine in spirit. Ethyl 4-(3-methyl-2 : 3-dihydro-4 : 5 - benzbenzthiazolylidene - 2) - 3 - methyl - 2 - cyano - 2 - butenoate, ethyl 4 - (3 - ethyl - 2 : 3 - dihydrobenzthiazolylidene - 2) - 3 - ethyl - 2 - cyano - 2-butenoate, and ethyl 4-(3-methyl-2 : 3-dihydrobenzthiazolylidene - 2) - 3 - methyl - 2 - cyano - 2 - butenoate are similarly prepared. Similar dyes may be prepared from quaternary salts of 2- and 4 - alkyl - quinolines, 2 - alkyl - benzoxazoles, 2 - alkyl - benzselenazoles, 2 : 3 : 3 - trialkylindolenines, and 2-alkyl-thiazolines, -selenazolines, and -oxazolines. Specification 642,514, [Group IV (b)], is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2572648A GB642515A (en) | 1948-10-02 | 1948-10-02 | Improvements in or relating to dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2572648A GB642515A (en) | 1948-10-02 | 1948-10-02 | Improvements in or relating to dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB642515A true GB642515A (en) | 1950-09-06 |
Family
ID=10232292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2572648A Expired GB642515A (en) | 1948-10-02 | 1948-10-02 | Improvements in or relating to dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB642515A (en) |
-
1948
- 1948-10-02 GB GB2572648A patent/GB642515A/en not_active Expired
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