CH157342A - Process for the preparation of a vat dye of the anthraquinone series. - Google Patents
Process for the preparation of a vat dye of the anthraquinone series.Info
- Publication number
- CH157342A CH157342A CH157342DA CH157342A CH 157342 A CH157342 A CH 157342A CH 157342D A CH157342D A CH 157342DA CH 157342 A CH157342 A CH 157342A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- nitrobenzene
- dye
- vat dye
- anthraquinone series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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 title 1
- 150000004056 anthraquinones Chemical class 0.000 title 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000975 dye Substances 0.000 claims description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 239000011230 binding agent Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellunz eines Fünenfarbstoffes der Anthraehinonreihe. Es wurde gefunden, dass man Küpen- farbstoffe von ausgezeichneten Echtheits eigenschaften erhält, wenn man Mono- oder Dicarbonsäuren des Diphenyläthers oder des Benzophenons oder deren Derivate und Sub- stitutionsprodukte in geeigneter Weise, *zum Beispiel in Form der Säurehalogenide, mit a - Aminoanthrachinonen,
beispielsweise 1- Aminoanthrachinon, 1-Amino-4- oder -5-ben- zoylaminoanthrachinon, 1-Amino-4-methogy- anthrachinon und andern kondensiert.
Die auf diese Weise erhältlichen Farb stoffe sind meist von gelber bis roter Nuance. Sie färben die tierische und pflanzliche Faser aus der Küpe in klaren Nuancen und besitzen gegenüber den bekannten, mittelst Arylmono,- carbonsäuren, z.
B. Benzoesäure oder Naphtoe- säure, erhältlichen Acylderivaten der Amino- anthrachinone sehr gutes Ziehvermögen und grosse Farbstärke. Durch diese Eigenschaften in Verbindung mit den vorzüglichen Echt heitseigenschaften stellen die neuen Farb- stoffe eine wertvolle Bereicherung der Küpenfarbstoffklasse dar.
Ihre Darstellung kann am einfachsten durch Kondensation der Säurehalogenide mit den entsprechenden Aminoanthrachinonen, zweckmässig in einem geeigneten Lösungs mittel, wie zum Beispiel Nitrobenzol, Chlor benzol, Trichlorbenzol oder Benzol, bei An- oder Abwesenheit eines säurebindenden Mit tels, erfolgen. Die Kondensation erfolgt zweckmässig in. der Wärme bei Temperaturen, die zwischen 80 und 210' C liegen.
Gegenstand vorliegenden Patentes ist ein Verfahren zur Darstellung eines Küpenfarb- stoffes, welches dadurch gekennzeichnet ist, dass man 1-Amino-anthrachinon mit 4.4'- Diphenyläther-dicarbonsäurechlorid konden siert. <I>Beispiel:</I> 10 Gewichtsteile 4 . 4'-Diphenylätherdicar- bonsäurechlorid (erhältlich durch Behandeln von 4. 4'-Diphenylätherdicarbonsäure - E. P.
Nr. 286,688: - mit Phosphorpentachlorid) und 15,2 Gewichtsteile 1-Aminoanthrachinon werden in 600 Gewichtsteilen Nitrobenzol mehrere Stunden auf etwa 120 C erhitzt. Der Farbstoff scheidet sich als gelber, kri stalliner Niederschlag aus. Er wird heiss ab gesaugt, erst mit warmem Nitrobenzol, schliesslich mit Alkohol gewaschen und ge trocknet. Die Ausbeute ist recht gut.
Der Farbstoff stellt ein gelb gefärbtes, kristal lines Produkt dar, das in Chlorbenzol, Nitro- benzol und Trichlorbenzol in der Wärme lös lich ist, sich in starker Schwefelsäure mit orangeroter Farbe löst und aus der rot ge färbten alkalischen Hydrosulfitlösung die tierische und pflanzliche Faser in klaren, grünstickig gelben Tönen von sehr guten Echtheitseigenschaften anfärbt.
Process for the preparation of a funnel dye of the anthraehinone series. It has been found that vat dyes with excellent fastness properties are obtained if mono- or dicarboxylic acids of diphenyl ether or benzophenone or their derivatives and substitution products are used in a suitable manner, * for example in the form of acid halides, with α-aminoanthraquinones,
for example 1-aminoanthraquinone, 1-amino-4- or -5-benzoylaminoanthraquinone, 1-amino-4-methogyanthraquinone and others condensed.
The dyes that can be obtained in this way are usually yellow to red. They color the animal and vegetable fibers from the vat in clear shades and have, compared to the known, means aryl mono, - carboxylic acids, z.
B. benzoic acid or naphthoic acid, acyl derivatives of amino anthraquinones available very good drawability and great color strength. Thanks to these properties in connection with the excellent fastness properties, the new dyes represent a valuable addition to the vat dye class.
The simplest way to prepare them is by condensing the acid halides with the corresponding aminoanthraquinones, conveniently in a suitable solvent, such as nitrobenzene, chlorobenzene, trichlorobenzene or benzene, in the presence or absence of an acid-binding agent. The condensation is expediently carried out in the heat at temperatures between 80 and 210 ° C.
The subject of the present patent is a process for the preparation of a vat dye which is characterized in that 1-amino-anthraquinone is condensed with 4,4′-diphenyl ether dicarboxylic acid chloride. <I> Example: </I> 10 parts by weight 4. 4'-diphenyl ether dicarboxylic acid chloride (obtainable by treating 4. 4'-diphenyl ether dicarboxylic acid - E.P.
No. 286,688: - with phosphorus pentachloride) and 15.2 parts by weight of 1-aminoanthraquinone are heated in 600 parts by weight of nitrobenzene at about 120 ° C. for several hours. The dye separates out as a yellow, crystalline precipitate. It is sucked off hot, first washed with warm nitrobenzene, then with alcohol and dried. The yield is quite good.
The dye is a yellow colored, crystalline product which is soluble in chlorobenzene, nitrobenzene and trichlorobenzene in the heat, dissolves in strong sulfuric acid with an orange-red color and from the red colored alkaline hydrosulphite solution the animal and vegetable fibers in dyes clear, greenish yellow shades with very good fastness properties.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE157342X | 1930-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH157342A true CH157342A (en) | 1932-09-30 |
Family
ID=5678586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH157342D CH157342A (en) | 1930-12-17 | 1931-12-15 | Process for the preparation of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH157342A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727044A (en) * | 1953-12-23 | 1955-12-13 | Interchem Corp | Yellow pigment |
-
1931
- 1931-12-15 CH CH157342D patent/CH157342A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727044A (en) * | 1953-12-23 | 1955-12-13 | Interchem Corp | Yellow pigment |
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