DE70659C - Process for the preparation of alkali-like azo dyes from a> i 04-dioxynaphthalene - Google Patents
Process for the preparation of alkali-like azo dyes from a> i 04-dioxynaphthaleneInfo
- Publication number
- DE70659C DE70659C DENDAT70659D DE70659DA DE70659C DE 70659 C DE70659 C DE 70659C DE NDAT70659 D DENDAT70659 D DE NDAT70659D DE 70659D A DE70659D A DE 70659DA DE 70659 C DE70659 C DE 70659C
- Authority
- DE
- Germany
- Prior art keywords
- dioxynaphthalene
- alkali
- preparation
- azo dyes
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000003513 alkali Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- 210000002268 Wool Anatomy 0.000 claims description 5
- 230000001808 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000001180 sulfating Effects 0.000 claims 1
- 239000000975 dye Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 240000007108 Fuchsia magellanica Species 0.000 description 1
- NIKFYOSELWJIOF-UHFFFAOYSA-O Fuchsine Chemical compound Cl.C1=C(N)C(C)=CC(C(=C2C=CC(=[NH2+])C=C2)C=2C=CC(N)=CC=2)=C1 NIKFYOSELWJIOF-UHFFFAOYSA-O 0.000 description 1
- ZUJURJDZOPMJPH-UHFFFAOYSA-M [Cl-].[N-]=[N+]=C1CC=CC=C1 Chemical compound [Cl-].[N-]=[N+]=C1CC=CC=C1 ZUJURJDZOPMJPH-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 238000005185 salting out Methods 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
- 238000003756 stirring Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Nach den Angaben der Patentschriften Nr. 54116, Nr. 57021 und Nr. 64017 entstehen werthvolle Azofarbstoffe, wenn Diazoverbindungen mit den Sulfosäuren des K1 ci4-Dioxynaphtalins combinirt werden.According to the information in patent specifications No. 54116, No. 57021 and No. 64017, valuable azo dyes are formed when diazo compounds are combined with the sulfonic acids of K 1 ci 4 -dioxynaphthalene.
Zu analogen gleichfalls technisch wichtigen Producten gelangt man, wenn man die aus Ci1 a4-Dioxynaphtalin durch Kuppeln mit Diazoverbindungen entstehenden Farbstoffe mit sulfirenden Mitteln behandelt.Analogous likewise technically important products are obtained if the dyes formed from Ci 1 a 4 -dioxynaphthalene by coupling with diazo compounds are treated with sulphurizing agents.
Die als Ausgangsproducte in diesem Verfahren benutzten Azofarbstoffe werden in üblicher Weise durch Kuppeln der betreffenden Diazoverbindungen mit Ct1 a4 - Dioxynaphtalin (Ann. 247, 356) erhalten, wie auch in den Patentschriften Nr. 51559 und Nr. 52958 beschrieben. The azo dyes used as starting products in this process are obtained in the customary manner by coupling the relevant diazo compounds with Ct 1 a 4 -dioxynaphthalene (Ann. 247, 356), as is also described in patent specifications No. 51559 and No. 52958.
Die Sulfirung selbst geschieht nach den üblichen Methoden unter Verwendung von monohydratischer, rauchender Schwefelsäure u. s. w.The sulfation itself takes place according to the usual methods using monohydric, fuming sulfuric acid and so on.
Die auf diese Weise durch Weitersulfiren dargestellten Producte sind hinsichtlich ihrer Zusammensetzung nicht mit denjenigen identisch, welche aus der gleichen Diazoverbindung durch Kuppelung mit Ct1 ct4 - Dioxynaphtalin - ctmonosulfosäure bezw. α, ^-Dioxynaphtalin -adisulfosäure oder U1 o^-Dioxynaphtalin-ß-disulfosäure gewonnen werden. Die so erhaltenen neuen Producte besitzen, hinsichtlich der Nuancen und der technischen Verwendung, mindestens den gleichen Werth, wie die in den Patentschriften Nr. 54116, Nr. 57021. und Nr. 64017 beschriebenen Farbstoffe.The products represented in this way by further sulfation are not identical with respect to their composition with those which are obtained from the same diazo compound by coupling with Ct 1 ct 4 -dioxynaphthalene-ct monosulfonic acid or. α, ^ -Dioxynaphthalene -a disulfonic acid or U 1 o ^ -Dioxynaphthalene-ß-disulfonic acid can be obtained. The new products obtained in this way have, in terms of nuances and technical use, at least the same value as the dyes described in Patents No. 54116, No. 57021. and No. 64017.
Das Verfahren wird durch folgendes Beispiel erläutert:The procedure is illustrated by the following example:
Farbstoff, erhalt en durchWeitersulfiren des aus diazotirtem Anilin Ci1 ^-Dioxynaphtalin entstehenden Zwischenproductes. Dyestuff obtained by further sulphuring of the intermediate product formed from diazotized aniline Ci 1 ^ -dioxynaphthalene.
Die aus 13 kg salzsaurem Anilin mittelst 7 kg Nitrit in salzsaurer Lösung erhaltene Diazobenzolchloridlösung läfst man unter Umrühren in ein, aus circa 30 kg essigsaurem Natron und 16 kg Ci1 Ci4-Dioxynaphtalin hergestelltes, mit viel Wasser unter Zusatz von Essigsäure angerührtes, Gemisch einfliefsen. Nach mehrstündigem Stehen ist die Kuppelung beendet. Der vollständig abgeschiedene Farbstoff wird abfiltrirt, mit Wasser ausgewaschen, geprefst und getrocknet. Das so dargestellte trockene Product wird in fein gesiebtem Zustande in die etwa 5 bis ι ο fache Gewichtsmenge monohydratische Schwefelsäure eingetragen und bei etwa 40 bis 50 ° so lange erwärmt, bis eine herausgenommene Probe sich leicht in Wasser mit fuchsinrother Farbe löst, die auf Zusatz von Alkali nicht mehr in Gelb umschlägt. Ist dieser Punkt erreicht, so giei'st man das SuI-firungsgemisch nach dem Erkalten in Wasser, fütrirt den eventuell nicht sulfirten Farbstoff ab und isolirt den sulfirten Farbstoff durch Aussalzen, Abfiltriren, Pressen und Trocknen.The diazobenzene chloride solution obtained from 13 kg of hydrochloric aniline by means of 7 kg of nitrite in hydrochloric acid solution is poured into a mixture made from about 30 kg of sodium acetate and 16 kg of Ci 1 Ci 4 -dioxynaphthalene, mixed with plenty of water with the addition of acetic acid, while stirring . After standing for several hours, the coupling is finished. The completely separated dye is filtered off, washed out with water, pressed and dried. The dry product thus represented is added in a finely sieved state to about 5 to ο times the amount by weight of monohydric sulfuric acid and heated at about 40 to 50 ° until a sample taken out dissolves easily in water with a fuchsia color, which is due to the addition of Alkali no longer turns yellow. Once this point has been reached, the mixture is poured into water after it has cooled down, any non-sulfated dye is removed and the sulfated dye is isolated by salting out, filtering out, pressing and drying.
Derselbe färbt gewöhnliche Wolle im sauren Bade fuchsinroth, chromgebeizte Wolle violettschwarz. It dyes ordinary wool in an acidic bath, fuchsin red, chrome-stained wool, purple-black.
Bemerkenswerth ist hierbei, dafs nach vorstehendem Beispiel bei kurzem Erhitzen zunächst ein Sulfoproduct entsteht, welches auf Zusatz von Alkalien seine Nuance nach Gelb verändert. Erst beim längeren Erhitzen diesesIt is noteworthy here that, according to the above example, initially with brief heating a sulfoproduct is produced which, when alkalis are added, turns its shade of yellow changes. Only when heated for a long time this
Farbstoffes mit monohydratischer Säure etc. bildet sich der alkalibestä'ndige Farbstoff. Erhitzt man zu lange, so verschwindet die Alkalibeständigkeit wieder und es entsteht ein Product, das durch Alkalien blau gefärbt wird.Dyestuff with monohydric acid etc. forms the alkali-resistant dyestuff. Heated if you go too long, the alkali resistance disappears again and a Product that is colored blue by alkalis.
In analoger Weise werden die übrigen Farbstoffe gewonnen, deren Prüfung bislang zu dem Resultate führte, dafs namentlich die folgenden Repräsentanten technisch äufserst wichtig sind, nämlich die aus den Diazoverbindungen der m- und p-Amidobenzolsulfosäure nach dem im vorstehenden Beispiele angegebenen Verfahren gewonnenen Producte, von denen ersteres mehr gelblich fuchsinrothe, letzteres mehr bläulich fuchsinrothe Nuancen auf gewöhnlicher Wolle erzeugt. Chromgebeizte Wolle wird von den drei Farbstoffen violettschwarz angefärbt.In an analogous manner, the other dyes are obtained, their testing so far to the Results that the following representatives in particular are technically extremely important, namely that from the diazo compounds of m- and p-amidobenzenesulfonic acid according to the im The products obtained by the methods given in the preceding examples, more of the former yellowish fuchsin-red, the latter more bluish fuchsin-red nuances on ordinary wool generated. Chrome-stained wool is colored purple-black by the three dyes.
Auch bei der Darstellung der beiden letztgenannten Farbstoffe entstehen zunächst Sulfosäuren, welche nicht alkalibeständig sind; nach längerem Erwärmen bilden sich die alkalibeständigen Producte, welche bei weiterem Erhitzen wieder alkaliunbeständig werden, so dafs sich allgemein das Ende des Sulfirungsprocesses aus den Nüancenänderungen, welche durch Alkalien hervorgerufen werden, leicht erkennen läfst.Also in the representation of the last two dyes, sulfonic acids are initially formed, which are not alkali-resistant; after prolonged heating, the alkali-resistant ones form Products which again become unstable to alkali on further heating, so that generally the end of the sulphurisation process is reached easily recognized from the changes in nuance caused by alkalis running.
Diese neuen Farbstoffe, welche hinsichtlich ihrer Nuancen nur geringe Unterschiede zeigen, sind durch ihr Egalisirungsvermögen und besonders durch ihre Alkaliechtheit den Producten der Patente Nr. 54116, Nr. 57021 und Nr. 64017 noch, überlegen. ■These new dyes, which show only minor differences in terms of their nuances, are the products by their ability to equalize, and especially by their fastness to alkali of patents No. 54116, No. 57021 and No. 64017 still, consider. ■
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE70659C true DE70659C (en) |
Family
ID=344023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT70659D Expired - Lifetime DE70659C (en) | Process for the preparation of alkali-like azo dyes from a> i 04-dioxynaphthalene |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE70659C (en) |
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0
- DE DENDAT70659D patent/DE70659C/en not_active Expired - Lifetime
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