DE281448C - - Google Patents
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- Publication number
- DE281448C DE281448C DENDAT281448D DE281448DA DE281448C DE 281448 C DE281448 C DE 281448C DE NDAT281448 D DENDAT281448 D DE NDAT281448D DE 281448D A DE281448D A DE 281448DA DE 281448 C DE281448 C DE 281448C
- Authority
- DE
- Germany
- Prior art keywords
- ecm
- solution
- naphtol
- amino
- diazo
- 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.)
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- 150000008049 diazo compounds Chemical class 0.000 claims description 5
- 239000000987 azo dye Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000004962 sulfoxyl group Chemical group 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- PZDXDOLQKQBWJV-UHFFFAOYSA-N 4-(nitromethoxy)aniline Chemical compound NC1=CC=C(OC[N+]([O-])=O)C=C1 PZDXDOLQKQBWJV-UHFFFAOYSA-N 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- HONMCSLFRKBQHG-UHFFFAOYSA-N 1,3-diamino-1,3-diphenylurea Chemical compound C=1C=CC=CC=1N(N)C(=O)N(N)C1=CC=CC=C1 HONMCSLFRKBQHG-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- QMIJLOSXZVDDAT-UHFFFAOYSA-N 3-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=CC(N)=CC(O)=C21 QMIJLOSXZVDDAT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- QFCSRGLEMDRBMN-UHFFFAOYSA-N N-(2-methylphenyl)nitramide Chemical class CC1=CC=CC=C1N[N+]([O-])=O QFCSRGLEMDRBMN-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N O-Anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 235000003846 Ricinus Nutrition 0.000 description 1
- 241000322381 Ricinus <louse> Species 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N Tolidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- 229940116362 Tragacanth Drugs 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- -1 that is Chemical compound 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Vr 281448 KLASSE 22a. GRUPPEVr 281448 CLASS 22a. GROUP
Verfahren zur Darstellung wasserunlöslicher Azofarbstoffe.Process for the preparation of water-insoluble azo dyes.
Patentiert im Deutschen Reiche vom 5. Dezember 1913 ab.Patented in the German Empire on December 5, 1913.
Es wurde gefunden, daß bei der Kombination solcher Diazoverbindungen, welche keine Sulfo- oder Carboxylgruppe enthalten, mit Acidyl - 2 - amino - 3 - naphtolen wasserunlösliche Azofarbstoffe entstehen, welche durch bemerkenswerte Echtheitseigenschaften ausgezeichnet sind. Als Diazoverbindungen kommen hier außer denjenigen aus Anilin und seinen Homologen und Substitutionsprodukten, wie o- und p-Anisidin, auch die aus Chlor- und Nitroderivaten, also Chlor- und Nitroanüinen, Chlor- und Nitrotoluidinen, Chlor- und Nitroanisidinen und auch aus α- und ß-Naphtylamin und Diaminobasen, wie z. B. Benzidin, Tolidin, Dianisidin, Diaminodiphenylharnstoff, und andere in Betracht.It has been found that when combining such diazo compounds, which none Contain sulfo or carboxyl group, with acidyl - 2 - amino - 3 - naphtholene insoluble in water Azo dyes are produced which are distinguished by their remarkable fastness properties are. As diazo compounds come here besides those from aniline and its homologues and substitution products, such as o- and p-anisidine, also those from chlorine and nitro derivatives, that is, chlorine and nitro anisidines, chlorine and nitrotoluidines, chlorine and nitro anisidines and also from α- and ß-naphthylamine and diamino bases, such as. B. Benzidine, Tolidine, Dianisidine, diaminodiphenylurea, and others are contemplated.
Azofarbstoffe aus 2-Acidylamino-3-naphtolen sind bisher noch nicht bekannt geworden. Gegenüber den von Witt in den Berichten der deutschen chemischen Gesellschaft Bd. 29, Seite 2949, und in der Patentschrift 93312 erwähnten unlöslichen Farbstoffen aus Acidyli-amino-4-naphtolen weisen die vorliegenden Farbstoffe wesentlich bessere Chlorechtheit auf.Azo dyes made from 2-acidylamino-3-naphtholes have not yet become known. Compared to Witt in the reports of the German chemical society Vol. 29, Page 2949, and in the patent 93312 mentioned insoluble dyes from Acidyli-amino-4-naphtholen the present dyes have significantly better chlorine fastness.
Die Farbstoffe können zur Darstellung von Pigmentfarbstoffen benutzt werden; man kann sie aber auch auf der Faser erzeugen nach den bei der Darstellung von Eisfarben in Betracht kommenden Verfahren. Verfährt man hierbei in der Weise, daß das mit alkalischen Lösungen der Acidyl-2-amino-3-naphtole imprägnierte Baumwollgut ohne zu trocknen mit den Diazoverbindungen entwickelt wird, so erhält man wesentlich kräftigere Färbungen als mit den bekannten Farbstoffen aus Acidyli-amino-4-naphtol. Die Kupplung kann je nach der Art der Diazokomponente in saurer, neutraler oder alkalischer Lösung geschehen.The dyes can be used to represent pigment dyes; one can but they also produce on the fiber according to the considerations for the representation of ice colors upcoming proceedings. If this is done in such a way that the impregnated with alkaline solutions of the acidyl-2-amino-3-naphtholes Cotton material is developed with the diazo compounds without drying, so the coloration obtained is much stronger than with the known dyes from Acidyli-amino-4-naphtol. The coupling can take place in an acidic, neutral or alkaline solution, depending on the type of diazo component.
Die aus 16,8 Teilen Nitröanisidin 4 · 1 · 2 (OCH3: N H2: N O2 ±= 1:2:4)The from 16.8 parts of nitroanisidine 4 · 1 · 2 (OCH 3 : NH 2 : NO 2 ± = 1: 2: 4)
in üblicher Weise dargestellte Diazoverbindung läßt man unter gutem Rühren in eine wässerige Suspension von 27 Teilen Benzoyl-2-amino-3-naphtol, bereitet durch Auflösen desselben in verdünnter Natronlauge und Wiederausfällen mit verdünnter Essigsäure, einlaufen. Der Farbstoff scheidet sich in roten Flocken ab, er wird nach Beendigung der Kombination abfiltriert, neutral gewaschen und vorteilhaft in Pastenform verwendet. Nach dem Trocknen bildet er ein lebhaft rotes Pulver. Bei der Verlackung gibt der Farbstoff rote Pigmentfarben von hervorragender ölechtheit.Diazo compound prepared in the usual way is allowed to pour into an aqueous one with thorough stirring Suspension of 27 parts of benzoyl-2-amino-3-naphtol, prepared by dissolving the same in dilute sodium hydroxide solution and reprecipitation with dilute acetic acid. Of the Dye is deposited in red flakes, it becomes after the combination is finished filtered off, washed neutral and advantageously used in paste form. After drying it forms a vivid red powder. When lacquered, the dye gives red pigment colors of excellent smoothness.
Erzeugung des Farbstoffes auf der Faser.Creation of the dye on the fiber.
Der Stoff wird geklotzt mit folgender Lösung:The fabric is padded with the following solution:
12 g Benzoyl-2-amino-3-naphtol, 20 ecm Natronlauge 340 Be, 25 g ricinusölsaures Natron werden zu einer Paste angeteigt, mit12 g benzoyl-2-amino-3-naphtol, 20 ecm sodium hydroxide solution 34 0 Be, 25 g ricinus oil acid sodium are made into a paste with
500 ecm kochendem Wasser gelöst und500 ecm of boiling water and dissolved
das Ganze auf 1 1 aufgefüllt. Der gut getrocknete Stoff wird bedruckt mit einem Gemisch von:the whole filled up to 1 1. The well-dried fabric is printed with a mixture of:
500 ecm Diazolösung, < 500 ecm diazo solution, <
500 g Tragantverdickung 1: 20, 25 ecm Natriumacetatlösung 1:1.500 g tragacanth thickener 1: 20, 25 ecm sodium acetate solution 1: 1.
Diazolösung:Diazo solution:
i6,8 g Nitroanisidin 4 · 1 · 2
(OCH3:NH2:NO2 = 1:2:4)16.8 g nitroanisidine 4x1x2
(OCH 3 : NH 2 : NO 2 = 1: 2: 4)
werden in bekannter Weise diazotiert, die Lösung mit 12,5. g schwefelsaurer Tonerde versetzt und auf 500 ecm aufgefüllt.are diazotized in a known manner, the solution with 12.5. g sulfuric acid clay added and filled to 500 ecm.
Nach dem Drucken wird die Ware getrocknet, gewaschen und bei 50 bis 70° geseift. Man erhält so satte rote Drucke.After printing, the goods are dried, washed and soaped at 50 to 70 °. In this way, deep red prints are obtained.
Erzeugt man den Farbstoff nach der Arbeitsweise der Patentschrift 268542 auf Baumwollgarn, so erhält man ein leuchtendes Rot von hervorragender Echtheit.If the dye is produced on cotton yarn according to the method of patent specification 268542, a bright red is obtained from excellent authenticity.
Das gut mit Soda oder Ätznatron ausgekochte, gebleichte oder rohe Baumwollgarn wird bei etwa 40 ° imprägniert mit einer Lösung von Benzoyl-2 · 3-ammonaphtol, deren Bereitung im Beispiel 1 beschrieben ist, scharf abgewunden und nach dem Erkalten in einem Färbebade von folgender Zusammensetzung gefärbt:The bleached or raw cotton thread boiled well with soda or caustic soda is impregnated at about 40 ° with a solution of benzoyl-2 · 3-ammonaphtol, whose Preparation is described in Example 1, sharply wound and after cooling in one Dyebath dyed of the following composition:
500 ecm Diazolösung werden mit
40 ecm Kupferchloridlösung 40 Be,
12 ecm Chromsäurelösung 1: 10 und
100 ecm essigsaurer Tonerde 12° Be gemischt
und kurz vor dem Färben500 ecm diazo solution are used with
40 ecm copper chloride solution 40 Be,
12 ecm chromic acid solution 1:10 and
100 ecm of acetic acid clay 12 ° Be mixed and just before dyeing
50 ecm essigsaures Natrium 1: 1 gelöst zugegeben.50 ecm of sodium acetic acid dissolved 1: 1 admitted.
Das Ganze wird auf ι 1 eingestellt.
Diazolösung:The whole thing is set to ι 1.
Diazo solution:
24 g Dianisidinbase werden mit
21 ecm Salzsäure 20 ° Be und
250 ecm kochendem Wasser gelöst, abgekühlt,
200 g Eis. und24 g of dianisidine base are added
21 ecm hydrochloric acid 20 ° Be and
250 ecm of boiling water dissolved, cooled,
200 g ice. and
10 ecm Salzsäure 20 Be zugegeben und 16 g Natriumnitrit, gelöst in
50 ecm Wasser, unter gütern^ Rühren einfließen gelassen, worauf auf 1 1
eingestellt wird.10 ecm hydrochloric acid 20 Be added and 16 g sodium nitrite, dissolved in
50 ecm of water, allowed to flow in while stirring well, whereupon it is set to 1 liter.
Nach dem Färben wird gut abgewunden, gut gewaschen und bei 70 bis 8o° geseift.After dyeing, it is well wound off, washed well and soaped at 70 to 80 °.
Man erhält so schöne rotstichig blaue Färbungen. Beautiful, reddish-tinged blue colorations are obtained in this way.
An Stelle von 2-Benzoylamino~3-naphtol können dessen Substitutionsprodukte, wie z. B. Halogenbenzoylamino-3-naphtol oder 2-Nitrobenzoylamino-3-naphtol oder andere Acidylderivate des 2 · 3-Aminonaphtols Verwendung finden, wie z. B. Acetylamino-3-naphtol, 3 · 31-Dioxy-2 · 21-dinaphtylharnstoff usw.Instead of 2-benzoylamino ~ 3-naphtol, its substitution products, such as. B. Halobenzoylamino-3-naphtol or 2-nitrobenzoylamino-3-naphtol or other acidyl derivatives of 2 · 3-aminonaphthol use, such as. B. Acetylamino-3-naphtol, 3 · 3 1 -dioxy-2 · 2 1 -dinaphtylurea etc.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE281448C true DE281448C (en) |
Family
ID=537189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT281448D Active DE281448C (en) |
Country Status (1)
| Country | Link |
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| DE (1) | DE281448C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7607825B2 (en) | 2005-08-29 | 2009-10-27 | Cmv Systems Gmbh & Co. Kg | Method and apparatus for monitoring the formation of deposits in furnaces |
-
0
- DE DENDAT281448D patent/DE281448C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7607825B2 (en) | 2005-08-29 | 2009-10-27 | Cmv Systems Gmbh & Co. Kg | Method and apparatus for monitoring the formation of deposits in furnaces |
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