GB638023A - Improvements in or relating to dyestuff intermediates - Google Patents
Improvements in or relating to dyestuff intermediatesInfo
- Publication number
- GB638023A GB638023A GB1479347A GB1479347A GB638023A GB 638023 A GB638023 A GB 638023A GB 1479347 A GB1479347 A GB 1479347A GB 1479347 A GB1479347 A GB 1479347A GB 638023 A GB638023 A GB 638023A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butadiene
- ethylthio
- toluenesulphonate
- etho
- benzthiazolyl
- 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 1
- 239000000543 intermediate Substances 0.000 title 1
- -1 hydroxalkyl Chemical group 0.000 abstract 14
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000002904 solvent Substances 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
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- HBBOGXAEKAVLGW-UHFFFAOYSA-N bis(ethylsulfanyl)methylsulfanylethane Chemical compound CCSC(SCC)SCC HBBOGXAEKAVLGW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000010992 reflux Methods 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
-
- 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
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
Dye intermediates are prepared by reacting a cyanine dye of the general formula <FORM:0638023/IV (b)/1> wherein R1 and R2 are each an alkyl, hydroxalkyl, aralkyl, or hydroxyaralkyl group, D1 and D2 are each the residue of a 5- or 6-membered heterocyclic nitrogen ring, n is 0 or 1, x is 1 or 2, and A is an acid radical, with an acid HX and a trithio-orthoformate of formula HC(SR3)3, wherein R3 is an alkyl or aralkyl group, in presence of a carboxylic acid or anhydride which is a solvent for the reactants. 1 - Ethylthio - 2 : 4 - di - a - quinolyl - 1 : 3-butadiene diethiodide is prepared by refluxing together 1 : 11 - diethyl - 2 : 21 - quinocarbocyanine iodide, toluene-p-sulphonic acid, triethyl trithio-orthoformate, and acetic anhydride, distilling off the solvent in vacuo, dissolving in ethyl alcohol, and pouring into aqueous KI solution. 1-Ethylthio-2 : 4-dibenzthiazolyl - 1 : 3 - butadiene monoethiodide monoetho - p - toluenesulphonate, 1 - ethylthio - 2 : 4-dibenzthiazolyl - 1 : 3 - butadiene di - etho - p-toluenesulphonate, 1 - methylthio - 2 : 4 - dibenzthiazolyl - 1 : 3 - butadiene di - etho - p-toluenesulphonate, 1 - benzylthio - 2 : 4 - dibenzthiazolyl - 1 : 3 - butadiene di - etho - p - toluenesulphonate, 1 - ethylthio - 2 : 4 - di - (51 - methyl-21 - benzthiazolyl - 1 : 3 - butadiene monoetho-p - toluenesulphonate monoethiodide, 1 - ethylthio - 2 : 4 - di - (51 - methyl - 21 - benzthiazolyl) 1 : 3 - butadiene di - ethiodide, 1 - ethylthio-2 : 4 - di - (51 - chloro - 21 - benzthiazolyl) - 1 : 3-butadiene di - etho - p - toluenesulphonate, 1 - ethylthio - 2 : 4 - di - (51 - chloro - 21 - benzthiazolyl) - 1 : 3 - butadiene di - ethiodide, 1-ethylthio - 2 : 4 - di - (41 : 51 - benzbenzthiazolyl) 1 : 3 - butadiene di - etho - p - toluenesulphonate, 1 - ethylthio - 2 : 4 - di - (41 : 51 - benzbenzthiazolyl) - 1 : 3 - butadiene diethiodide, 1-benzylthio - 2 : 4 - di - (41 : 51 - benzbenzthiazolyl) - 1 : 3 - butadiene di - etho - p - toluenesulphonate, 1 - ethylthio - 2 : 4 - di - a - quinolyl-1 : 3 - butadiene di - ethobromide, 1 - ethylthio-2 : 4 - di - a - quinolyl - 1 : 3 - butadiene monoethobromide mono - etho - 21 - naphthalenesulphonate, 1 - ethylthio - 2 : 4 - di - g - quinolyl-1 : 3 - butadiene monoethobromide mono - etho-p - toluenesulphonate, 1 - ethylthio - 2 : 4 - di-g - quinolyl - 1 : 3 - butadiene diethiodide, 1 - ethylthio - 2 : 4 - dibenzelenazolyl - 1 : 3-butadiene di - etho - p - toluenesulphonate, 1-ethylthio - 2 : 6 - di - (31 : 31 - dimethylindolenyl) 1 : 3 : 5 - hexatriene monomethiodide monometho - p - toluenesulphonate, 1 - ethylthio - 2 : 6-di - (51 - methyl - 21 - benzthiazolyl) - 1 : 3 : 5-hexatriene mono - ethiodide mono - etho - p-toluenesulphonate, and 1 - ethulthio - 2 : 6 - di-(51 - chloro - 21 - benzthiazolyl) - 1 : 3 : 5-hexatriene mono - ethiodide mono - etho - p-toluenesulphonate are similarly prepared. Specification 638,024, [Group IV (c)], is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1479347A GB638023A (en) | 1947-06-04 | 1947-06-04 | Improvements in or relating to dyestuff intermediates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1479347A GB638023A (en) | 1947-06-04 | 1947-06-04 | Improvements in or relating to dyestuff intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB638023A true GB638023A (en) | 1950-05-31 |
Family
ID=10047578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1479347A Expired GB638023A (en) | 1947-06-04 | 1947-06-04 | Improvements in or relating to dyestuff intermediates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB638023A (en) |
-
1947
- 1947-06-04 GB GB1479347A patent/GB638023A/en not_active Expired
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