DE238979C - - Google Patents
Info
- Publication number
- DE238979C DE238979C DENDAT238979D DE238979DA DE238979C DE 238979 C DE238979 C DE 238979C DE NDAT238979 D DENDAT238979 D DE NDAT238979D DE 238979D A DE238979D A DE 238979DA DE 238979 C DE238979 C DE 238979C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- parts
- aminoanthraquinone
- indanthrene
- dyes
- 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
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- 239000000975 dye Substances 0.000 claims description 6
- 235000019239 indanthrene blue RS Nutrition 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UHOKSCJSTAHBSO-UHFFFAOYSA-N Indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 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
- LKPDQKDPTIERGP-UHFFFAOYSA-N 2-amino-1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(N)=C2C LKPDQKDPTIERGP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HTBVSSIRTUHJQP-UHFFFAOYSA-N 2-(aminomethyl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CN)=CC=C3C(=O)C2=C1 HTBVSSIRTUHJQP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 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
- C09B5/44—Azines of the anthracene series
- C09B5/46—Para-diazines
- C09B5/48—Bis-anthraquinonediazines (indanthrone)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
238979 KLASSE 22b. GRUPPE238979 CLASS 22b. GROUP
Verfahren zur Darstellung von Anthracenfarbstoffe^Process for the preparation of anthracene dyes ^
Patentiert im Deutschen Reiche vom 9. April 1910 ab. Patented in the German Empire on April 9, 1910 .
In der Patentschrift 129845 ist ein Verfahren zur Darstellung eines blauen, als Indanthren oder Indanthrenblau bekannten Küpen^ farbstoffe beschrieben, darin bestehend, daß 2-Aminoanthrachinon mit Kalihydrat verschmolzen und der entstandene Farbstoff aus der mit Luft behandelten Schmelze abgeschieden wird. Das Indanthren läßt sich auch nach anderen Methoden gewinnen. So kann man es auch erhalten durch Behandeln von 2-Aminoanthrachinon mit sauren Oxydationsmitteln (Patente 139633 und 141355) oder aus ι · 2 -Aminohalogen- bzw. 2 -Amino-i · 3-dihalogenanthrachinonen durch geeignete Kondensation (Patente 158287 und 158474) oder auch aus i-Aminoanthrachinon durch saure Mittel oder Metallsalze (Patente 186636 und 186637) °der durch Kondensation von 1 > 2-Diaminoanthrachinon mit Alizarin (Patent 178130).In the patent specification 129845 a process for the preparation of a blue, known as indanthrene or indanthrene blue vat is described dyes, consisting in that 2-aminoanthraquinone is fused with potassium hydrate and the resulting dye is deposited from the air-treated melt. The indanthrene can also be obtained by other methods. It can also be obtained by treating 2-aminoanthraquinone with acidic oxidizing agents (patents 139633 and 141355) or from ι · 2 -aminohalogen- or 2-amino-i · 3-dihalogenanthraquinones by suitable condensation (patents 158287 and 158474) or also from i-aminoanthraquinone by acidic agents or metal salts (patents 186636 and 186637) ° he d by condensation of 1> 2-diaminoanthraquinone with alizarin (Patent 178,130).
Es wurde nun gefunden, daß man neue Indanthrenfarbstoffe von wertvollen Eigenschaften erhält, wenn man Aminoanthrachinone, welche eine oder mehrere Methylgruppen im Anthrachinonkern enthalten, nach den beschriebenen Methoden in die Farbstoffe überführt. Selbstverständlich können gleichzeitig sonstige Substituenten und auch eine Methylgrüppe in der Aminogruppe" anwesendIt has now been found that new indanthrene dyes of valuable properties can be obtained obtained when aminoanthraquinones, which have one or more methyl groups contained in the anthraquinone nucleus, converted into the dyes by the methods described. Of course, other substituents and also a methyl group can be used at the same time in the amino group "present
Die erhaltenen methylierten Indanthrene zeichnen sich durch wertvolle, vom Indanthren selbst zum Teil stark verschiedene Nuancen und durch hervorragende Färbe- und Echtheitseigenschaften aus.The methylated indanthrenes obtained are distinguished by valuable indanthrene even in some cases very different nuances and through excellent coloring and fastness properties the end.
ι Teil 2 · 3 - Aminomethylanthrachinon, 40 Teile Eisessig und 3 Teile Bleisuperoxyd werden während 3 Stunden zum Sieden erhitzt. Nach dem Erkalten wird abgesaugt und zur Entfernung des Bleis mit verdünnter Salzsäure ausgekocht. Das 3 · 3'-Dimethylindanthren kann durch Umkristallisieren aus viel Nitrobenzol in ganz reiner Form erhalten werden. Es stellt ein blaugrünes Kristallpulver dar, das in organischen Lösungsmitteln sehr schwer löslich ist. Mit alkalischem Hydrosulfit bildet es eine blaue Küpe, aus der Baumwolle in blauen Tönen angefärbt wird, die beim Waschen in ein Blaugrün übergehen.ι Part 2 · 3 - aminomethylanthraquinone, 40 parts of glacial acetic acid and 3 parts of lead peroxide heated to boiling for 3 hours. After cooling, suction is performed and dilute hydrochloric acid is used to remove the lead boiled out. The 3 · 3'-Dimethylindanthren can be recrystallized from a lot Nitrobenzene can be obtained in completely pure form. It represents a blue-green crystal powder which is very sparingly soluble in organic solvents. With alkaline hydrosulphite it forms a blue vat from which cotton is dyed in blue tones that turn blue-green when washed.
Auf gleiche Art kann man z. B. 6- (bzw. 7-) Methyl - 2 - aminoanthrachinon in 6 · 6'- (bzw. 7 · 7'-) Dimethylindanthren überführen.In the same way you can z. B. 6- (or 7-) methyl - 2 - aminoanthraquinone in 6 · 6'- (or Convert 7 · 7'-) dimethylindanthrene.
In 4 Teile Ätzkali wird bei 2500 1 Teil 6- (bzw. 7-) Methyl-2-aminoanthrachinon eingetragen und unter Rühren 1Z2 Stunde auf 2600 erhitzt. Man kocht die erkaltete Schmelze mit Wasser auf, filtriert und wäscht aus. Das 6 · 6'- (bzw. 7 · 7-) Dimethylindanthren läßt sich ebenfalls aus viel Nitrobenzol kristallisieren und bildet dann ein dunkelblaues Kristallpulver von ähnlichen Löslichkeitseigenschäften wie 3 · 3'-Dimethylindanthren.1 part of 6- (or 7-) methyl-2-aminoanthraquinone is introduced into 4 parts of caustic potash at 250 0 and heated to 260 0 for 1 Z 2 hours with stirring. The cooled melt is boiled with water, filtered and washed out. The 6x6'- (or 7x7-) dimethylindanthrene can also be crystallized from a large amount of nitrobenzene and then forms a dark blue crystal powder with solubility properties similar to those of 3x3'-dimethylindanthrene.
6060
6565
Aus der blauen alkalischen Küpe erhält man nach dem Waschen dunkelblaue Färbungen von großer Deckkraft. After washing, the blue alkaline vat gives dark blue dyeings of great covering power.
Beispiel III.Example III.
io Teile i-Brom-a-am'ino-s-methylanthrachinon, 120 Teile Naphtalin, ι Teil Kupferoxyd, 5 Teile entwässertes Natriumacetat und 4 Teile Magnesia werden während 4 bis 5 Stunden zum Sieden erhitzt. Der entstandene blaugrüne Farbstoff wird heiß abgesaugt, mit Spi ritus, verdünnter Salzsäure und Wasser heiß gewaschen. Das Produkt ist identisch mit dem nach Beispiel I erhaltenen.io parts of i-bromo-a-amino-s-methylanthraquinone, 120 parts of naphthalene, ι part of copper oxide, 5 parts of dehydrated sodium acetate and 4 parts Magnesia are heated to the boil for 4 to 5 hours. The blue-green dye formed is filtered off with suction while hot, with Spi ritus, dilute hydrochloric acid and water washed hot. The product is identical to that obtained according to Example I.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE238979C true DE238979C (en) |
Family
ID=498457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT238979D Active DE238979C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE238979C (en) |
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- DE DENDAT238979D patent/DE238979C/de active Active
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