DE194254C - - Google Patents
Info
- Publication number
- DE194254C DE194254C DE1905194254D DE194254DA DE194254C DE 194254 C DE194254 C DE 194254C DE 1905194254 D DE1905194254 D DE 1905194254D DE 194254D A DE194254D A DE 194254DA DE 194254 C DE194254 C DE 194254C
- Authority
- DE
- Germany
- Prior art keywords
- oxy
- thionaphthene
- sulfur
- carboxylic acid
- dye
- 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 - Lifetime
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N Benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000001044 red dye Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000003568 thioethers Chemical group 0.000 description 2
- 150000003574 thionaphthenes Chemical class 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 210000004080 Milk Anatomy 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001603 reducing Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 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
- C09B7/00—Indigoid dyes
- C09B7/10—Bis-thionapthene indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Phenylthioglykol-o-carbonsäure geht durch Wasser- bzw. durch Wasser- und Kohlensäureabspaltung in die 3-Oxy(i)thionaphten-2-carbonsäure bzw. das 3-Oxy(i)thionaphten selbst über. Durch Einwirkung oxydierender Mittel entsteht aus den Thionaphtenderivaten ein roter schwefelhaltiger Farbstoff. The phenylthioglycol-o-carboxylic acid goes by splitting off water or by splitting off water and carbonic acid into 3-oxy (i) thionaphthene-2-carboxylic acid or the 3-oxy (i) thionaphthene itself. The thionaphthene derivatives are formed by the action of oxidizing agents a red sulfur-containing dye.
Es wurde nun gefunden, daß sogar Schwefel die Oxydation bewirkt. Die Reaktion wird vorteilhaft in Gegenwart von Alkalien ausgeführt, wobei naturgemäß Alkalisulfide sich bilden. Es gelingt trotzdem, die Thionaphtenderivate vollständig in den Farbstoff überzuführen, was bei der anerkannten Reduktionswirkung der Sulfide nicht vorherzusehen war.It has now been found that even sulfur causes the oxidation. The reaction will advantageously carried out in the presence of alkalis, with naturally alkali sulfides form. Nevertheless, it is possible to completely convert the thionaphthene derivatives into the dye, which could not have been foreseen with the recognized reducing effect of sulphides.
19 kg 3-Oxy(i)thionaphten-2-carbonsäure werden in etwa 50 kg Natronlauge19 kg of 3-oxy (i) thionaphthene-2-carboxylic acid are about 50 kg of caustic soda
g gg g
400 Be. und Wasser gelöst und mit 16 kg Schwefel, vorteilhaft in Form von Schwefelmilch, versetzt. Man erhitzt das Reaktionsgemisch, es färbt sich nach kurzer Zeit rot, wobei sich der gebildete Farbstoff abscheidet.40 0 Be. and water dissolved and mixed with 16 kg of sulfur, advantageously in the form of sulfur milk. The reaction mixture is heated; after a short time it turns red, the dye formed separating out.
Sobald die Oxydation beendet ist, filtriert man und wäscht aus.As soon as the oxidation has ended, it is filtered and washed out.
Falls bei der Ausführung des Verfahrens sich in dem Filtrate des Farbstoffs etwas von seiner Leukoverbindung befinden sollte, so kann sie isoliert oder in der üblichen Weise oxydiert werden.In case there is some dye in the filtrate when carrying out the process of its leuco compound, it can be isolated or in the usual way Way to be oxidized.
In dem Beispiel kann die 3-Oxy(l)thionaphten-2-carbonsäure durch die äquivalente Menge 3-Oxy(i)thionaphten ersetzt werden.In the example, the 3-oxy (l) thionaphthene-2-carboxylic acid replaced by the equivalent amount of 3-oxy (i) thionaphtene.
15 kg 3-Oxy(i)thionaphten werden mit 5 kg Schwefel innig gemischt und allmählich erhitzt. Unter Schwefelwasserstoffentwicklung geht das 3-Oxy(i)thionaphten in den roten schwefelhaltigen Farbstoff über.15 kg of 3-oxy (i) thionaphtene weigh 5 kg Sulfur intimately mixed and gradually heated. With evolution of hydrogen sulfide the 3-oxy (i) thionaphthene passes into the red, sulfur-containing dye.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT35898D AT35898B (en) | 1905-12-22 | 1907-05-23 | Process for the production of a red dye. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE194254C true DE194254C (en) |
Family
ID=457410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1905194254D Expired - Lifetime DE194254C (en) | 1905-12-22 | 1905-12-22 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE194254C (en) |
-
1905
- 1905-12-22 DE DE1905194254D patent/DE194254C/de not_active Expired - Lifetime
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