CH148497A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH148497A CH148497A CH148497DA CH148497A CH 148497 A CH148497 A CH 148497A CH 148497D A CH148497D A CH 148497DA CH 148497 A CH148497 A CH 148497A
- Authority
- CH
- Switzerland
- Prior art keywords
- vat dye
- vat
- production
- blue
- sulfuric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 229910001510 metal chloride Inorganic materials 0.000 claims description 3
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- -1 cliin-oline Chemical compound 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass man einen wert- vol#len Küpenfarbstoff erhält, wenn man das durch Brümieren von Dibenzanthron erhält- lielie Dibro-mdibenzantliro-n mit einem wasser freien, Chlor abgebenden Metallelilorid be handelt.
Für die Durchführung des Verfahrens be sonders geeignete Metallchloride sind die Chloride des Eisens, Aluminiums, Antimons, Quecksilbers ete. und deren Gemische. Vor- teilha.ft arbeitet man in Gegenwart von schmelzpunkterniedrigenden Zusätzen, wie Alkali- und Erdalkalisalze, oder von die Wirksamkeit deir MetalleIlloride nicht be- einträchti--enden Lösungs- oder Suspensions,- mitteln, wie Halogenbenzole,
Halogennapli- taline, Benzophenon, Nitrobenzol, Cliin-olin, Pyridin, Collidin ete. Man kann auch Ka talysatoren, wie Jod und andere Meta.11oide, oder deren Verbindungen, mitverwenden.
Das Reaktionsprodukt, ein Ch.lordibrom- dibenza,nthro#n, löst sich in konzentrierter Schwefelsäure mit violetter Farbe und lie fert aus grünblauer Küpe marineblaue Fär bungen, die neben allgemein sehr guten son stigen Eigenschaften gegenüber dem Aus- gangsmateria,1 den Vorteil besitzen, bezüg lich der Niiance von der Färbetemperatur unabhängig zu sein.
<I>Beispiel<B>1:</B></I> <B>62</B> Teile Dibromdibenzanthron werden in 2000 Teilen TriGlilorbenzol unter Rühren auf 140<B>' C</B> erhitzt. Bei dieser Temperatur trägt man 480 Teile wasserfreies Eiselichlorid ein und rührt bei 140 bis<B>150<I>\</I></B> C solange,<B>bis</B> eine entnommene Probe -eine grünblaue Kü- Penlösung liefert, aus der Baumwolle in was- sereGhten Tönen -efärbt wird.
Darauf lässt man abkühlen, destilliert das Trielilorbenzol, gegebenenfalls mit Wasserdampf oder hezw. und unter vermindertem Druck,<B>ab,</B> und ar beitet in der üblich-en Weise auf.
Der rohe Farbstoff kann aus organischen Lösungsmitteln, zum Beispiel Nitrobenzol, oder aus Schwefelsäure umkristallisiert, oder auch nach andern Methoden, zum Beispiel durch Behandeln in Pastenform mit Oxy dationsmitteln, zum Beispiel Natriumhypo- ohlorit, gereinigt werden.
<I>Beispiel 2:</I> <B>31</B> Teile Dibromdibenzanthron werden bei 120'<B>C</B> in eine Schmelze von<B>300</B> TQi- len Aluminiumehlorid, <B>60</B> Teilen Kochsalz und<B>3</B> Teilen Jod unter Rühren eingetragen und mehrere Stunden bei<B>180' C</B> gerührt. Nacli Beendigung der Salzsäureentwicklung giesst man die Sollmelze in verdünnte Salz säure oder Schwefelsäure, saugt heiss ab, wäselit neutral und trocknet.
Process for the production of a vat dye. It has been found that a valuable vat dye is obtained if the dibenzanthrone obtained by browning dibenzanthrone is treated with an anhydrous, chlorine-releasing metal fluoride.
Metal chlorides which are particularly suitable for carrying out the process are the chlorides of iron, aluminum, antimony and mercury. and their mixtures. It is advantageous to work in the presence of additives that lower the melting point, such as alkali and alkaline earth salts, or of solvents or suspending agents that do not impair the effectiveness of the metal chloride, such as halobenzenes,
Halogennapli- taline, benzophenone, nitrobenzene, cliin-oline, pyridine, collidine etc. You can also use catalysts, such as iodine and other meta.11oids, or their compounds.
The reaction product, a Ch.lordibromodibenza, nthro # n, dissolves in concentrated sulfuric acid with a violet color and delivers navy blue colors from a green-blue vat which, in addition to generally very good other properties, have the advantage over the starting material to be independent of the dyeing temperature with regard to the Niiance.
<I>Example<B>1:</B> </I> <B> 62 </B> parts of dibromodibenzanthrone are heated in 2000 parts of tri-glilobenzene to 140 <B> 'C </B> with stirring. 480 parts of anhydrous iron chloride are introduced at this temperature and the mixture is stirred at 140 to 150 C until a sample taken - a green-blue bowl - Provides a pen solution from which cotton is dyed in water-resistant shades.
It is then allowed to cool, the trielilobenzene is distilled, optionally with steam or hezw. and under reduced pressure, <B> off, </B> and work on in the usual way.
The crude dye can be recrystallized from organic solvents, for example nitrobenzene, or from sulfuric acid, or can also be purified by other methods, for example by treatment in paste form with oxidizing agents, for example sodium hypochlorite.
<I> Example 2: </I> <B> 31 </B> parts of dibromodibenzanthrone are at 120 '<B> C </B> in a melt of <B> 300 </B> TQiles of aluminum chloride, < B> 60 parts of table salt and 3 parts of iodine are added with stirring and the mixture is stirred for several hours at 180 ° C. After the development of hydrochloric acid has ended, the nominal melt is poured into dilute hydrochloric acid or sulfuric acid, suctioned off while hot, washed neutral and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE148497X | 1929-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH148497A true CH148497A (en) | 1931-07-31 |
Family
ID=5672740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH148497D CH148497A (en) | 1929-04-27 | 1930-04-16 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH148497A (en) |
-
1930
- 1930-04-16 CH CH148497D patent/CH148497A/en unknown
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