DE176019C - - Google Patents
Info
- Publication number
- DE176019C DE176019C DENDAT176019D DE176019DA DE176019C DE 176019 C DE176019 C DE 176019C DE NDAT176019 D DENDAT176019 D DE NDAT176019D DE 176019D A DE176019D A DE 176019DA DE 176019 C DE176019 C DE 176019C
- Authority
- DE
- Germany
- Prior art keywords
- water
- anthracene
- benzanthrones
- benzanthrone
- glycerol
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 13
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 235000011187 glycerol Nutrition 0.000 claims description 5
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 claims description 4
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims 1
- 150000001454 anthracenes Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000984 vat dye Substances 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- IWRGJSINRVRSPA-UHFFFAOYSA-N anthracene-1,9-diol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=CC3=CC2=C1 IWRGJSINRVRSPA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
- C09B3/04—Preparation by synthesis of the nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Gemäß den Patenten 171939 und 176018 werden ß-Aminoanthrachinon und seine (nicht ο-ständig dihydroxylierten) Derivate sowie auch Anthrachinon und Anthrachinonsulfosäuren und deren Reduktionsprodukte mit Glycerin kondensiert zur Darstellung von Verbindungen einer neuen Körperklasse der »Benzanthrone«. Das Benzanthron C17H10O (aus Oxyanthranol z. B. und Glycerin dargestellt) und die meisten seiner Derivate zeigen die wichtige Eigenschaft, bei der Behandlung mit kaustischen Alkalien ausgezeichnete Küpenfarbstoffe von hervorragenden Echtheitseigenschaften zu liefern.According to patents 171939 and 176018, ß-aminoanthraquinone and its (not ο-permanently dihydroxylated) derivatives as well as anthraquinone and anthraquinone sulfonic acids and their reduction products are condensed with glycerol to produce compounds of a new body class of "benzanthrones". Benzanthrone C 17 H 10 O (prepared from oxyanthranol, for example, and glycerol) and most of its derivatives show the important property of providing excellent vat dyes with excellent fastness properties when treated with caustic alkalis.
Es wurde nun die weitere Beobachtung gemacht, daß für die »Benzanthronsynthese« die Gegenwart eines ß-Aminoanthrachinon- oder Anthrachinonrestes nicht erforderlich ist, daß vielmehr auch das sauerstofffreie Anthracen selbst sich mit Glycerin zu Benzanthronen kondensieren läßt.Another observation was made that for the "synthesis of benzanthrone" the presence of a ß-aminoanthraquinone or anthraquinone residue is not required, that rather the oxygen-free anthracene itself with glycerine to form benzanthrones lets condense.
50 kg Anthracen, 98prozentig, werden in 1500 kg Schwefelsäure von 62° Be. eingetragen und versetzt mit 100 kg Glycerin; diese Mischung wird langsam auf 100 bis 1100C. erhitzt und so lange bei dieser Temperatur gehalten, bis das Anthracen verschwunden ist. Die braunrot gefärbte Schmelze wird nach dem Erkalten in Wasser gegossen, mit Kochsalz versetzt und filtriert.50 kg anthracene, 98 percent, are in 1500 kg sulfuric acid of 62 ° Be. entered and mixed with 100 kg of glycerol; this mixture is slowly heated to 100 to 110 ° C. and kept at this temperature until the anthracene has disappeared. The brown-red colored melt is poured into water after cooling, mixed with common salt and filtered.
Das getrocknete Kondensationsprodukt stelltThe dried condensation product represents
*) Früheres Zusatzpatent 176018.*) Former additional patent 176018.
ein graugrünes Pulver dar; es besteht der Hauptsache nach aus einem wasserunlöslichen und aus einem wasserlöslichen Körper. Der wasserunlösliche Anteil liefert beim Umkristallisieren aus Alkohol einen in feinen gelben Nadeln kristallisierenden Körper vom Schmelzpunkt 1700 .C. Es ist dies der Schmelzpunkt des »Benzanthrons« (Beispiel 1 der Patentschrift 176018); auch in seinen Reaktionen stimmt er völlig mit jenem überein. Seine Lösung in konzentrierter Schwefelsäure ist leuchtend orangerot mit ebensolcher Fluorescenz; beim Verschmelzen mit kaustischem Kali erhält man einen wasserunlöslichen Farbstoff, welcher die pflanzliche Faser aus der Küpe violett anfärbt.represents a gray-green powder; it consists mainly of a water-insoluble and a water-soluble body. The water-insoluble fraction provides a crystallized in fine yellow needles body of melting point 170 0 .C when recrystallized from alcohol. This is the melting point of "benzanthrone" (example 1 of patent 176018); In his reactions too, he completely agrees with that one. Its solution in concentrated sulfuric acid is bright orange-red with the same fluorescence; when fused with caustic potash, a water-insoluble dye is obtained, which stains the vegetable fiber from the vat purple.
Der wasserlösliche Teil des Rohprodukts löst sich in rohem Zustand in konzentrierter Schwefelsäure mit orangeroter Farbe und ebensolcher Fluorescenz; auch dieses Produkt liefert beim Verschmelzen mit kaustischen Alkalien einen violetten Küpenfarbstoff.The water-soluble part of the crude product dissolves in the raw state in concentrated form Sulfuric acid with an orange-red color and fluorescence; also this product When fused with caustic alkalis, it produces a purple vat dye.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE176019C true DE176019C (en) |
Family
ID=440612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT176019D Active DE176019C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE176019C (en) |
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0
- DE DENDAT176019D patent/DE176019C/de active Active
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