CH232516A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH232516A CH232516A CH232516DA CH232516A CH 232516 A CH232516 A CH 232516A CH 232516D A CH232516D A CH 232516DA CH 232516 A CH232516 A CH 232516A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- dye
- vat dye
- bromo
- vat
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 239000000984 vat dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- KJEICVAXCBDOSH-UHFFFAOYSA-N 3-bromonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C=C(Br)C(C(=O)O)=CC2=C1 KJEICVAXCBDOSH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/26—Carbazoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Nüpenfarbstoifes. Es wurde gefunden, dass man einen wert vollen Küpenfarbstoff der Anthrachinonreihe erhält, wenn man das 1(2'-Brom)-3'-naph- thoylamino-4-ss-naphthylaminoanthrachinon mit einem carbazolierend wirkenden Mittel behandelt.
Der Farbstoff ist identisch mit dem des schweiz. Patentes Nr. 228137. <I>Beispiel:</I> In 300 Gewichtsteile Schwefelsäure von 86 7o Gehalt trägt man unter Kühlung und gutem Rühren 20 Gewichtsteile 1(2'-Brom) 3'-naphthoylamino-4-ss-naphthylaminoanthra- chinon ein, lässt die Temperatur allmählich auf 15 C steigen und hält bei der Tempera tur, solange noch Ausgangsmaterial nach weisbar ist.
Hierauf gibt man auf Eiswasser, rührt 7 Gewichtsteile Natriumnitrit ein und erwärmt 1/2 Stunde auf 80 C. Der Farbstoff wird dann isoliert und gegebenenfalls durch Behandeln mit einem Lösungsmittel, wie Ni- trobenzol, gereinigt. Der in rotbraunen Kri stallen vorliegende Farbstoff löst sich in kon zentrierter Schwefelsäure grün, in Lösungs mitteln, zum Beispiel Chinolin, rotorange.
Beim Eingiessen dieser Lösung in verdünnte Salzsäure erhält man eine leicht verküpbare Paste, die aus rotbrauner Küpe braune Fär bungen liefert, die gelbstichiger sind, als die mit dem bromfreien Produkt hergestellten.
Das für die Umsetzung benötigte Aus gangsmaterial lässt sich beispielsweise er halten durch Kondensation von 1-Amino-4- bromanthrachinon-2-sulfonsäure mit ss-Naph- thylamin in wässriger Lösung, Abspaltung der Sulfogruppe und Acylierung der freien Aminogruppe mit 2-Brom-3-naphthoesäure in bekannter Weise.
Process for the production of a nub dye. It has been found that a valuable vat dye of the anthraquinone series is obtained if the 1 (2'-bromo) -3'-naphthoylamino-4-ss-naphthylaminoanthraquinone is treated with a carbazolizing agent.
The dye is identical to that of Switzerland. Patent No. 228137. <I> Example: </I> 20 parts by weight of 1 (2'-bromo) 3'-naphthoylamino-4-ss-naphthylaminoanthraquinone are added to 300 parts by weight of sulfuric acid with a content of 86,7o, with cooling and thorough stirring one, lets the temperature rise gradually to 15 C and holds at that temperature as long as the starting material is still detectable.
This is then poured into ice water, 7 parts by weight of sodium nitrite are stirred in and the mixture is heated to 80 ° C. for 1/2 hour. The dye is then isolated and, if necessary, purified by treatment with a solvent such as nitrobenzene. The dye, which is present in red-brown crystals, dissolves green in concentrated sulfuric acid and red-orange in solvents such as quinoline.
When this solution is poured into dilute hydrochloric acid, an easily vettable paste is obtained which, from the reddish-brown vat, delivers brown colorations that are more yellowish than those made with the bromine-free product.
The starting material required for the reaction can, for example, be obtained by condensing 1-amino-4-bromoanthraquinone-2-sulfonic acid with β-naphthylamine in aqueous solution, splitting off the sulfo group and acylating the free amino group with 2-bromo-3 -naphthoic acid in a known manner.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE232516X | 1938-10-06 | ||
| CH227982T | 1939-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH232516A true CH232516A (en) | 1944-05-31 |
Family
ID=25727169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH232516D CH232516A (en) | 1938-10-06 | 1939-10-03 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH232516A (en) |
-
1939
- 1939-10-03 CH CH232516D patent/CH232516A/en unknown
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