GB620802A - Improvements in or relating to dyestuffs - Google Patents
Improvements in or relating to dyestuffsInfo
- Publication number
- GB620802A GB620802A GB223947A GB223947A GB620802A GB 620802 A GB620802 A GB 620802A GB 223947 A GB223947 A GB 223947A GB 223947 A GB223947 A GB 223947A GB 620802 A GB620802 A GB 620802A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- iodide
- aralkyl
- cyanotrimethinecyanine
- group
- 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 9
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 8
- 150000003839 salts Chemical group 0.000 abstract 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- BFIRHDQVLGCNMT-UHFFFAOYSA-N 2-(3-methyl-3a,4-dihydro-1,3-benzothiazol-2-ylidene)acetonitrile Chemical compound C(#N)C=C1SC=2C(N1C)CC=CC2 BFIRHDQVLGCNMT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 2
- -1 cyanomethyl Chemical class 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- PQNQOHDLTYFBHE-UHFFFAOYSA-N 1-ethyl-2h-quinoline Chemical compound C1=CC=C2N(CC)CC=CC2=C1 PQNQOHDLTYFBHE-UHFFFAOYSA-N 0.000 abstract 1
- VORLTHPZWVELIX-UHFFFAOYSA-N 1-methyl-2h-quinoline Chemical compound C1=CC=C2N(C)CC=CC2=C1 VORLTHPZWVELIX-UHFFFAOYSA-N 0.000 abstract 1
- KAXCQPGHOGBDHH-UHFFFAOYSA-N 2-(1-ethyl-3,4-dihydroquinolin-2-ylidene)acetonitrile Chemical compound C(#N)C=C1N(C2=CC=CC=C2CC1)CC KAXCQPGHOGBDHH-UHFFFAOYSA-N 0.000 abstract 1
- ULMLYTLFCDSIRK-UHFFFAOYSA-N 2-(3-ethyl-3a,4-dihydro-1,3-benzothiazol-2-ylidene)acetonitrile Chemical compound C(#N)C=C1SC=2C(N1CC)CC=CC2 ULMLYTLFCDSIRK-UHFFFAOYSA-N 0.000 abstract 1
- TZSMBECTPMJVJS-UHFFFAOYSA-N 2-(3-methyl-6-nitro-3a,4-dihydro-1,3-benzothiazol-2-ylidene)acetonitrile Chemical compound [N+](=O)([O-])C=1C=C2C(N(C(S2)=CC#N)C)CC1 TZSMBECTPMJVJS-UHFFFAOYSA-N 0.000 abstract 1
- 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
- IITIZHOBOIBGBW-UHFFFAOYSA-N 3-ethyl-2h-1,3-benzothiazole Chemical compound C1=CC=C2N(CC)CSC2=C1 IITIZHOBOIBGBW-UHFFFAOYSA-N 0.000 abstract 1
- PXDAXYDMZCYZNH-UHFFFAOYSA-N 3-methyl-2h-1,3-benzothiazole Chemical compound C1=CC=C2N(C)CSC2=C1 PXDAXYDMZCYZNH-UHFFFAOYSA-N 0.000 abstract 1
- VCVACUXPDLCBHF-UHFFFAOYSA-N 3-methyl-2h-1,3-benzoxazole Chemical compound C1=CC=C2N(C)COC2=C1 VCVACUXPDLCBHF-UHFFFAOYSA-N 0.000 abstract 1
- TXSUCPGQFRTONT-UHFFFAOYSA-N 5-chloro-3-methyl-2h-1,3-benzothiazole Chemical compound C1=C(Cl)C=C2N(C)CSC2=C1 TXSUCPGQFRTONT-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 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
- 238000010992 reflux Methods 0.000 abstract 1
- 125000000854 selenoether group Chemical group 0.000 abstract 1
- 150000003568 thioethers Chemical class 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
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
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
- C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
Abstract
Dye intermediates of the formula <FORM:0620802/IV (b)/1> wherein R1 is an alkyl or aralkyl group, D1 is the residue of a 5- or 6-membered heterocyclic ring, and n is 0 or 1, or the corresponding cyanomethyl derivative of the alkyl or aralkyl quaternary salt, with an alkyl or aralkyl quaternary salt of a 5- or 6-membered heterocyclic N compound having in the a - or g -position to the quaternary N atom an alkyl, aralkyl, or aryl thioethervinyl, thioetherbutadienyl, selenoethervinyl, or selenoetherbutadienyl group or a group of formula -(CH=CH)mNH2 (where m is 1, 2, or 3), or an N-acyl, N-aryl, or N-acylaryl derivative thereof, are prepared by reacting the corresponding alkyl or aralkyl quaternary salt of the heterocyclic N compound having a reactive halogen atom or thioether or selenoether group attached in the a - or g -position to the quaternary N atom with cyanacetic acid. 2-Cyanomethylene-3-methyldihydrobenzthiazole is prepared by fusing together 2 - methylmercaptobenzthiazole and methyl p-toluenesulphonate, adding cyanacetic acid and pyridine, and boiling. 2-Cyanomethylene - 3 - ethyldihydrobenzthiazole, 6 - nitro-2 - cyanomethylene - 3 - methyldihydrobenzthiazole, and 2 - cyanomethylene - 1 - ethyldihydroquinoline are similarly prepared. Samples have been furnished under Sect. 2 (5) of the Acts, of the dyes 2-(3-ethylbenzthiazole) - 21 - (1 : 3 : 3 - trimethylindolenine) - a - cyanotrimethinecyanine iodide and p 2-(3-ethylbenzthiazole) - 41 - (1 - ethylquinoline) - a - cyanoheptamethinecyanine iodide. Specification 552,921 is referred to.ALSO:Cyanine dyes are prepared by condensing together an intermediate of the general formula <FORM:0620802/IV (c)/1> wherein R1 is an alkyl or aralkyl group, D1 is the residue of a 5- or 6-membered heterocyclic ring, and n is 0 or 1, or the corresponding cyanomethyl derivative of the alkyl or aralkyl quaternary salt with an alkyl or aralkyl quaternary salt of a 5- or 6-membered heterocyclic N compound having in the a - or g -position to the quaternary N atom an alkyl, aralkyl, or aryl thioethervinyl, thioetherbutadienyl, selenoethervinyl or selenoetherbutadienyl group or a group of formula -(CH=CH)mNH2 (where m is 1, 2 or 3) or an N-acyl, N-aryl or N-acylaryl derivative thereof. 2 - (3 - Methylbenzthiazole) - 21 - (3 - methyl - 5 - chlorobenzthiazole)-cyanotrimethinecyanine iodide is prepared by refluxing together 2-ethylmercaptovinyl)-5-chlorobenzthiazole metho-p-toluenesulphonate, 2-cyanmethylene-3-methyl-dihydrobenzthiazole and pyridine, and pouring into aqueous KI solution. Bis-2-(3-ethylbenzthiazole)-a -cyanotrimethinecyanine iodide, 2-(1-methylquinoline) - 21 - (1 : 3 : 3 - trimethylin - dolenine) - a - cyanotrimethinecyanine iodide and 2 - (1 - methylquinoline) - 21 - (3 - methylbenz - oxazole) - a - cyanotrimethinecyanine iodide are similarly prepared. Samples have been furnished under Sect. 2(5) of 2 - (3 - ethylbenzthiazole) - 21 - (1 : 3 : 3 - tri - methylindolenine) - cyanotrimethinecyanine iodide and of 2-(3-ethylbenzthiazole)-41-(1-ethylquinoline) - cyanoheptamethinecyanine iodide. Specification 552,921 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB223947A GB620802A (en) | 1947-01-24 | 1947-01-24 | Improvements in or relating to dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB223947A GB620802A (en) | 1947-01-24 | 1947-01-24 | Improvements in or relating to dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB620802A true GB620802A (en) | 1949-03-30 |
Family
ID=9736046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB223947A Expired GB620802A (en) | 1947-01-24 | 1947-01-24 | Improvements in or relating to dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB620802A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2993907A (en) * | 1955-05-27 | 1961-07-25 | Bayer Ag | Cyanomethylene indoline derivatives |
| US3090782A (en) * | 1958-03-04 | 1963-05-21 | Bayer Ag | Process for the production of cyanine dyestuffs |
| EP0003565A1 (en) * | 1978-02-02 | 1979-08-22 | Montedison S.p.A. | Disperse dyes based on isatin derivatives and process for their preparation, and their use for dyeing and printing synthetic fibres |
-
1947
- 1947-01-24 GB GB223947A patent/GB620802A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2993907A (en) * | 1955-05-27 | 1961-07-25 | Bayer Ag | Cyanomethylene indoline derivatives |
| US3090782A (en) * | 1958-03-04 | 1963-05-21 | Bayer Ag | Process for the production of cyanine dyestuffs |
| EP0003565A1 (en) * | 1978-02-02 | 1979-08-22 | Montedison S.p.A. | Disperse dyes based on isatin derivatives and process for their preparation, and their use for dyeing and printing synthetic fibres |
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