DE253762C - - Google Patents
Info
- Publication number
- DE253762C DE253762C DENDAT253762D DE253762DA DE253762C DE 253762 C DE253762 C DE 253762C DE NDAT253762 D DENDAT253762 D DE NDAT253762D DE 253762D A DE253762D A DE 253762DA DE 253762 C DE253762 C DE 253762C
- Authority
- DE
- Germany
- Prior art keywords
- dye
- oxy
- directly
- thionaphthene
- nitroaceanthrenequinone
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N Benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000001005 nitro dye Substances 0.000 claims description 2
- -1 nitroaceanthrenequinone Chemical compound 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- 238000007664 blowing Methods 0.000 claims 1
- 238000004043 dyeing Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- 229960000583 Acetic Acid Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 1
- VHWWGPALAQGYDH-UHFFFAOYSA-N 3-nitroacenaphthylene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)C3=C2C1=CC=C3[N+](=O)[O-] VHWWGPALAQGYDH-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- YAIBDWAANBTYIA-UHFFFAOYSA-N aceanthrylene-1,2-dione Chemical compound C1=CC=C2C(C(C3=O)=O)=C4C3=CC=CC4=CC2=C1 YAIBDWAANBTYIA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 235000019221 dark chocolate Nutrition 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09B7/12—Other thionaphthene indigos
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 253762 KLASSE 22 e. GRUPPE- M 253762 CLASS 22 e. GROUP
in BASEL.in Basel.
Verfahren zur Darstellung von Küpenfarbstoffen.Process for the preparation of vat dyes.
Zusatz zum Patent 205377 vom τ7· Januar 1907.*)Addition to patent 205377 from τ 7 January 1907. *)
Patentiert im Deutschen Reiche vom 2. Mai 1911 ab. Längste Dauer: 16. Januar 1922.Patented in the German Empire on May 2, 1911. Longest duration: January 16, 1922.
Bei der weiteren Ausbildung des durch das Patent 205377 geschützten Verfahrens wurde gefunden, daß man durch Kondensation von Nitroaceanthrenchinon mit 3-Oxy(i)thionaphten und nachfolgende partielle Reduktion einen Farbstoff erhält, welcher ungeheizte Baumwolle aus der Küpe in vollen, echten, schokoladenbraunen Tönen anfärbt. Dieses Resultat war überraschend, weil einerseits der Farbstoff ausAceanthrenchinon und3-Oxy(i)thionaphten nur farbschwache und waschunechte Färbungen liefert (vgl. auch Berl. Berichte 44, S. 854). Andererseits ist das entsprechende Kondensationsprodukt aus Nitroacenaphtenchinon nicht chlorecht, während der nach vorliegendem Verfahren erhältliche Farbstoff Färbungen von vorzüglicher Chlorechtheit liefert.In the further development of the process protected by patent 205377 was found that by condensation of nitroaceanthrenchinon with 3-oxy (i) thionaphten and subsequent partial reduction to obtain a dye which unheated cotton colors from the vat in full, genuine, chocolate-brown tones. This result was surprising because, on the one hand, the dye consists of aceanthrenequinone and 3-oxy (i) thionaphthene only provides weak and non-washable stains (cf. also Berl. Reports 44, p. 854). On the other hand, the corresponding condensation product from nitroacenaphthenequinone is not chlorine-resistant, while the dye obtainable by the present process is colorations of excellent chlorine fastness.
Das zur Kondensation angewandte Nitroaceanthrenchinon wird aus dem in den Berliner Berichten 44, S. 209 beschriebenen Aceanthrenchinon durch Nitrieren in konzentrierter schwefelsaurer Lösung mit der für ein Mononitroderivat berechneten Menge Mischsäure in der üblichen Weise erhalten und das Produkt ev. durch Umkristallisieren aus Eisessig gereinigt. Es ist darin ziemlich schwer löslich, kristallisiert daraus in glasigen Krusten und hat keinen scharfen Schmelzpunkt, indem es lange vor der Verflüssigung sintert und sich bräunt.The nitroaceanthrenequinone used for condensation becomes from the aceanthrenchinon described in the Berlin reports 44, p. 209 by nitrating in concentrated sulfuric acid solution with the amount of mixed acid calculated for a mononitro derivative obtained in the usual way and the product possibly by recrystallization from glacial acetic acid cleaned. It is rather difficult to dissolve in it and crystallizes from it in glassy crusts and does not have a sharp melting point by sintering and long before liquefaction tans.
6 Teile dieses Nitrokörpers werden in 500 Volumteilen Eisessig kochend gelöst und mit der äquivalenten Menge technischer 3-Oxy(i)thionaphten-2-karbonsäure, ebenfalls in Eisessig gelöst, versetzt. Zu der kochenden Lösung läßt man nach und nach 50 Volumteile konzentrierte Salzsäure fließen, wobei sich der Farbstoff als orangefarbener, kristallinischer Niederschlag rasch abscheidet. Er wird abfiltriert, gewaschen, mit Sprit zu einem Brei verrieben und nach Zusatz von Schwefelnatrium in geringem Überschuß auf dem Dampfbad erwärmt. Hierbei schlägt die orangebraune Farbe der Suspension in ein dunkles Schokoladebraun um. Nach dem Absaugen und Waschen liegt der Farbstoff in unmittelbar küpbarer Form vor. In konzentrierter Schwefelsäure ist er mit grüner Farbe löslich, mit Natronlauge und Hydrosulfit gibt er eine grünliche Küpe. Die Reduktion des •Nitrofarbstoffs geht unter obigen Bedingungen im wesentlichen nur bis zum Aminokörper.6 parts of this nitro body are dissolved in 500 parts by volume of glacial acetic acid and at the boil with the equivalent amount of technical 3-oxy (i) thionaphthene-2-carboxylic acid, also dissolved in glacial acetic acid, added. Gradually 50 parts by volume are added to the boiling solution concentrated hydrochloric acid flow, whereby the dye turns out to be orange, crystalline Precipitation separates quickly. It is filtered off, washed, with fuel to one Triturated into a pulp and, after adding sodium sulphide in a slight excess, on the Steam bath heated. The orange-brown color of the suspension changes to a dark chocolate brown. After suction and washing, the dye is in an immediately kneadable form. In concentrated Sulfuric acid is soluble with green color, with caustic soda and hydrosulfite there he a greenish vat. The reduction of the • nitro dye takes place under the above conditions essentially only up to the amino body.
*) Frühere Zusatzpatente: 206647, 2I°8'3> 2IO9°5> 211696 und 212870. (iff)'? Sfr4)*) Former additional patents: 206647, 2I ° 8'3> 2IO 9 ° 5> 211696 and 212870. (iff) '? S f r4)
Claims (1)
Weitere Ausbildung des durch Patent 205377 geschützten Verfahrens zur Darstellung von Küpenfarbstoffen, dadurch gekennzeichnet, daß man 3-Oxy (1) thionaphten mit Nitroaceanthrenchinon kondensiert und hierauf das Kondensationsprodukt mit Reduktionsmitteln behandelt.Patent-A ν saying:
Further development of the process for the preparation of vat dyes, which is protected by patent 205377, characterized in that 3-oxy (1) thionaphthene is condensed with nitroaceanthrenequinone and the condensation product is then treated with reducing agents.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE253762C true DE253762C (en) |
Family
ID=512012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT253762D Active DE253762C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE253762C (en) |
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0
- DE DENDAT253762D patent/DE253762C/de active Active
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