CH285010A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH285010A CH285010A CH285010DA CH285010A CH 285010 A CH285010 A CH 285010A CH 285010D A CH285010D A CH 285010DA CH 285010 A CH285010 A CH 285010A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- mol
- production
- blue
- diamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000009835 boiling Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 238000005574 benzylation reaction Methods 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 239000012897 dilution medium Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- UVUZEMDPEFGUPY-UHFFFAOYSA-N 1,8-diamino-4,5-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C([N+]([O-])=O)C=CC(N)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2N UVUZEMDPEFGUPY-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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- -1 dinitro compound Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 280186. Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass ein wertvoller Küpenfarbstoff hergestellt werden kann, wenn man 1 Mol 7.,8-Diamino-4,5-di-(2'-anthrachino- nylamino)-anthrachinon mit 2 Mol eines ben- zoylierenden Mittels umsetzt.
Der neue Farbstoff stellt ein grünblaues Pulver dar, das sich in konzentrierter Schwe felsäure mit reinblauer Farbe löst. Er färbt aus rotbrauner Küpe auf Baumwolle ein blau stichiges Olivgrün von hervorragenden Echt heitseigenschaften.
Das dem vorliegenden Verfahren als Aus gangsstoff dienende 1,8-Diamino-4,5-di-(2'-an- thrachinonylamino)-anthrachinon kann durch Umsetzen von 1 Mol 1,8-Diamino-4,5-dinitro- anthrachinon mit 2 Mol eines ss-Halogen- ant.hraehinons und nachträgliche Rechtktion der Dinitroverbindung zum Diamin erhalten werden.
Als benzoylierende Mittel können beispiels weise Halogenide der Benzolsäure, insbeson dere Benzoylehlorid, verwendet werden, und die Benzoylierung erfolgt vorteilhaft in einem hochsiedenden Lösungs- bzw. Verdünnungs mittel.
Beispiel: In feingepulvertem Zustande werden 16,4 Teile 1,8-Diamino-4,5-dinitro-anthrachinon, 29,1 Teile 2-Chloranthrachinon, 10,6 Teile wasserfreies Natriumearbonat, 5 Teile Magne- siumoayd und 3 Teile Kupferehlorür mit 230 Teilen Naphthalin vermischt. Man erhitzt und rührt die Schmelze so lange unter leichtem Sieden, bis die Ausgangsprodukte versehwun- den sind. Darin lässt man auf l.60 abkühlen, verdünnt mit 120 Teilen Monochlorbenzol und rührt eine Stunde bei 140 bis 150 . Nach dem Abkühlen auf etwa. 90 wird abgesaugt.
Der Rückstand wird durch Behandeln mit 1lono- chlorbenzol, Alkohol, verdünnter Salzsäure und Wasser gereinigt und dann getrocknet. Die Ausbeute beträgt etwa 60 bis 701/o der Theorie.
22,2 Teile so erhaltenes und feingepulver- tes 1,8-Dinitro-4,5-di-(2'-antliraehinonylamino)- anthrachinon werden in 400 Teilen Nitroben- zol auf etwa<B>1.00</B> bis l.10 erwärmt. Man gibt zuerst 8 Teile und nach einer Stunde nochmals 4 Teile Hydrazinhydrat (von 95 % Gehalt) zu. Das entstandene 1,
8-Diamino-4,5-di-(2'-anthra- chinonylamino)-anthraehinon wird heiss abge saugt, mit Nitrobenzol und mit Alkohol gewa schen und dann getrocknet. Die Ausbeute be trägt 90 bis 95 1/a der Theorie.
13,6 Teile feingepulvertes 1,8-Diamino- 4, 5-di - (2'-anthrachinonylamino) - anthraehinon werden in 400 Teilen Nitrobenzol unter Rüh ren auf 195 erhitzt. Man gibt 7 Teile Benzoyl- ehlorid zu und rührt eine Stunde unter leich tem Sieden. Nach dem Abkühlen wird abge saugt, der Rückstand mit Nitrobenzol und mit Alkohol gewaschen und dann getrocknet. Die Ausbeute beträgt etwa 70 1/a der Theorie.
<B> Additional patent </B> to main patent no. 280186. Process for the production of a vat dye. It has been found that a valuable vat dye can be produced by reacting 1 mol of 7th, 8-diamino-4,5-di- (2'-anthraquinonylamino) anthraquinone with 2 mol of a benzoylating agent.
The new dye is a green-blue powder that dissolves in concentrated sulfuric acid with a pure blue color. From a reddish brown vat on cotton it dyes a blue olive green with excellent fastness properties.
The 1,8-diamino-4,5-di- (2'-anthrachinonylamino) anthraquinone serving as the starting material for the present process can by reacting 1 mol of 1,8-diamino-4,5-dinitro anthraquinone with 2 mol of a ss-halogen ant.hraehinons and subsequent rectification of the dinitro compound to the diamine can be obtained.
As benzoylating agents, halides of benzene acid, in particular benzoyl chloride, can be used, for example, and the benzoylation is advantageously carried out in a high-boiling solvent or diluent.
Example: In a finely powdered state, 16.4 parts of 1,8-diamino-4,5-dinitro-anthraquinone, 29.1 parts of 2-chloroanthraquinone, 10.6 parts of anhydrous sodium carbonate, 5 parts of magnesium oxide and 3 parts of copper chloride with 230 Parts of naphthalene mixed. The melt is heated and stirred with gentle boiling until the starting products have disappeared. It is left to cool to 1.60, diluted with 120 parts of monochlorobenzene and stirred for one hour at 140 to 150. After cooling down to about. 90 is sucked off.
The residue is purified by treatment with monochlorobenzene, alcohol, dilute hydrochloric acid and water and then dried. The yield is about 60 to 701 / o of theory.
22.2 parts of 1,8-dinitro-4,5-di- (2'-antliraehinonylamino) anthraquinone thus obtained and finely powdered are reduced to about 1.00 to 1 in 400 parts of nitrobenzene. 10 heated. First 8 parts and after one hour a further 4 parts of hydrazine hydrate (95% content) are added. The resulting 1,
8-Diamino-4,5-di- (2'-anthraquinonylamino) -anthraehinone is sucked off hot, washed with nitrobenzene and with alcohol and then dried. The yield be 90 to 95 1 / a of theory.
13.6 parts of finely powdered 1,8-diamino-4,5-di - (2'-anthraquinonylamino) - anthraehinone are heated to 195 in 400 parts of nitrobenzene with stirring. 7 parts of benzoyl chloride are added and the mixture is stirred for one hour with gentle boiling. After cooling, it is filtered off with suction, the residue is washed with nitrobenzene and with alcohol and then dried. The yield is about 70 1 / a of theory.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH280186T | 1949-07-21 | ||
| CH285010T | 1949-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH285010A true CH285010A (en) | 1952-08-15 |
Family
ID=25731981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH285010D CH285010A (en) | 1949-07-21 | 1949-07-21 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH285010A (en) |
-
1949
- 1949-07-21 CH CH285010D patent/CH285010A/en unknown
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