DE177622C - - Google Patents
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- Publication number
- DE177622C DE177622C DENDAT177622D DE177622DA DE177622C DE 177622 C DE177622 C DE 177622C DE NDAT177622 D DENDAT177622 D DE NDAT177622D DE 177622D A DE177622D A DE 177622DA DE 177622 C DE177622 C DE 177622C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- brown
- sulfonic acid
- black
- 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.)
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- 239000000975 dye Substances 0.000 claims description 17
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 150000004780 naphthols Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000002268 Wool Anatomy 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011449 brick Substances 0.000 description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
- QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 3
- 240000000358 Viola adunca Species 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 230000001808 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WZPLEIAOQJXZJX-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(O)=CC2=C1 WZPLEIAOQJXZJX-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-Aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- ABJQKDJOYSQVFX-UHFFFAOYSA-N 4-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=C(O)C2=C1 ABJQKDJOYSQVFX-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- 210000004369 Blood Anatomy 0.000 description 1
- HQRFSHUZRPBXHC-UHFFFAOYSA-N C(C)(=O)C1=C(C(=C(C=C1)O)N)N Chemical compound C(C)(=O)C1=C(C(=C(C=C1)O)N)N HQRFSHUZRPBXHC-UHFFFAOYSA-N 0.000 description 1
- 241000394591 Hybanthus Species 0.000 description 1
- 229940018564 M-PHENYLENEDIAMINE Drugs 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- XOGQRLFPXMSUQS-UHFFFAOYSA-N OC1=C(C(=C(C=C1)C(C1=CC=CC=C1)=O)N)N Chemical compound OC1=C(C(=C(C=C1)C(C1=CC=CC=C1)=O)N)N XOGQRLFPXMSUQS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000020127 ayran Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
KLASSE 22 a. GRUPPECLASS 22 a. GROUP
in FRANKFURT a. M.in FRANKFURT a. M.
Im Patent 167257 wurden Monoazofarbstoffe beschrieben, welche man durch Kuppeln der Diazoverbindung der o-o-Acetyldiaminophenol-p-sulfosäure mit verschiedenen Komponenten erhält. Diese Monoazofarbstoffe besitzen als nachchromierbare Wollfarbstoffe einen hohen, technischen Wert. In weiterer Bearbeitung der Derivate der Diaminophenolsulfosäure wurde nun gefunden, daß auch die einseitig benzoylierte Diaminophenolsulfosäure: In patent 167257 monoazo dyes were described which can be obtained by coupling the diazo compound of o-o-acetyldiaminophenol-p-sulfonic acid with different components. These monoazo dyes have wool dyes that can be post-chromed a high technical value. In further processing of the derivatives of diaminophenolsulfonic acid it has now been found that the diaminophenolsulfonic acid benzoylated on one side also:
NHC6H5CONHC 6 H 5 CO
SO3HSO 3 H
diazotiert und mit den verschiedenartigsten Komponenten gekuppelt, Monoazofarbstoffe liefert, die — auf der Faser mit Chromsalzen behandelt — in ebenso echte Lacke übergehen wie die Farbstoffe aus der Acetyldiaminophenolsulfosäure. Ebenso wie letztere zeichnen sich die neuen Monoazofarbstoffe aus Benzoyldiaminophenolsulfosäure vorteilhaft aus durch vorzügliche Egalisierungsfähigkeit beim Färben.diazotized and coupled with a wide variety of components, monoazo dyes which - treated with chromium salts on the fiber - in just as real lacquers pass like the dyes from acetyldiaminophenol sulfonic acid. Just like the latter the new monoazo dyes from benzoyldiaminophenolsulfonic acid are advantageous due to its excellent leveling ability when dyeing.
Die Darstellung der Farbstoffe sei an folgenden Beispielen erläutert:The representation of the dyes is illustrated by the following examples:
30,8 Teile Benzoyldiaminophenolsulfosäure werden in Wasser unter Zusatz der berechneten Menge Alkali gelöst, die Lösung mit Eis gekühlt und mit 35 Teilen Salzsäure 2i° Be. versetzt, wobei die Benzoyldiaminophenolsulfosäure in fein verteilter Form ausfällt. Man diazotiert nun unter Zusatz von 7,2 Teilen technischen Nitrit, bis alle Benzoyldiaminophenolsulfosäure als Diazoverbindung klar in Lösung gegangen ist und läßt die Diazolösung in eine sodaalkalisch gehaltene Auflösung von 16 Teilen Dioxynaphtalin ·— 1:5 in 24 Teilen Natronlauge von 400 Be. einlaufen. Die Farbstoffverbindung ist bald beendet und der fertige Farbstoff wird durch Aussalzen aus der blauviolett gefärbten Kuppelungsflüssigkeit ausgefällt, filtriert und getrocknet. Er stellt ein schwarzes, bronzeglänzendes Pulver dar, das sich in Wasser mit blauvioletter Farbe löst. Auf Zusatz von Natronlauge zur wäßrigen Lösung schlägt die Farbe nach rotviolett um. Die Lösung des Farbstoffs in konzentrierter Schwefelsäure sieht grün aus. In saurem Bade auf Wolle gefärbt liefert der Farbstoff ein Rotbraun, das vorzüglich egalisiert, bei sehr gut erschöpftem Farbbade. Nachchromiert schlägt die Nuance in ein tiefes blaustichiges Schwarz um, das in bezug auf30.8 parts of benzoyldiaminophenolsulphonic acid are dissolved in water with the addition of the calculated amount of alkali, the solution is cooled with ice and treated with 35 parts of hydrochloric acid 21 ° Be. added, whereby the benzoyldiaminophenolsulfonic acid precipitates in finely divided form. Now diazotising with the addition of 7.2 parts technical nitrite, has gone to all Benzoyldiaminophenolsulfosäure as diazo clear in solution and allowing the diazo in a sodaalkalisch held resolution of 16 parts Dioxynaphtalin · - 1: 5 in 24 parts of sodium hydroxide 40 0 Be. come in. The dye compound is soon terminated and the finished dye is precipitated by salting out the blue-violet colored coupling liquid, filtered and dried. It is a black, shiny bronze powder that dissolves in water with a blue-violet color. When sodium hydroxide is added to the aqueous solution, the color changes to red-violet. The solution of the dye in concentrated sulfuric acid looks green. Dyed on wool in an acid bath, the dye produces a reddish-brown which levels out excellently, if the color bath is very exhausted. After chroming, the nuance turns into a deep blue-tinged black, which in relation to
Walk-, Blut-, Wasch- und Säurekochechtheit den weitestgehenden Anforderungen der Echtwollfärberei entspricht.Milling, blood, washing and acid boiling fastness meet the most extensive requirements of real wool dyeing is equivalent to.
30,8 Teile Benzoyldiaminophenolsulfosäure werden, wie unter Beispiel I beschrieben, diazotiert, in schwach sodaalkalischer Lösung mit 11 kg m-Phenylendiamin gekuppelt, der Farbstoff durch Kochsalz gefällt und getrocknet. Er ist ein braunes Pulver, das sich leicht mit gelbbrauner Farbe in Wasser30.8 parts of benzoyldiaminophenolsulfonic acid are diazotized as described in Example I, coupled in a weakly alkaline solution with 11 kg of m-phenylenediamine, the Dye precipitated through table salt and dried. It is a brown powder that turns slightly yellow-brown in color in water
Farbstoff aus diazotrierter Benzoyldiaminophenolsulfosäure undDiazotrated benzoyldiaminophenol sulfonic acid and dye
Resorzin Resorcinol
α- Naphtol α- naphtol
ß-Naphfol ...'. ß-Naphfol ... '.
α-Oxynaphtoesäure α-oxynaphtoic acid
β-Oxynaphtoesäure. ,β-oxynaphtoic acid. ,
m - Tolüylendiamin m - tolylenediamine
m-Aminophenol m-aminophenol
2 · 7-Dioxynaphtalin 2 · 7-dioxynaphthalene
ι · 4-Naphtolsulfosäure ι · 4-naphthol sulfonic acid
ι · 5-Naphtolsulfosäure ι · 5-naphthol sulfonic acid
2 · 6-Naphtolsulfosäure 2 x 6-naphthol sulfonic acid
2 · 7-Naphtolsulfosäure 2 x 7-naphthol sulfonic acid
2 · 5 · 7-Aminonaphtolsulfosäure 2x5x7-aminonaphthol sulfonic acid
ι · 8 · 4- Aminonaphtolsulfosäure ....'., 1-8-3 · 6-Aminonaphtoldisulfosäure ., ι · 8 · 3 · 6 -Dioxynaphtalindisulfosäureι · 8 · 4- aminonaphthol sulfonic acid .... '., 1-8-3 · 6-aminonaphthol disulfonic acid., ι · 8 · 3 · 6-dioxynaphthalene disulfonic acid
Phenylmethylpyrazolon Phenylmethylpyrazolone
Phenylmethylpyrazolonkarbonsäure Phenylmethylpyrazolonsulfosäure . . . .Phenylmethylpyrazolone carboxylic acid Phenylmethylpyrazolone sulfonic acid. . . .
löst. Seine Lösung in konzentrierter Schwefelsäure ist orangerot. Er färbt auf Wolle in saurem Bade ein Gelbbräun; die Farbbäder werden gut erschöpft. Beim Nachchromieren resultiert ein gelbstichiges tiefes Braun, dessen Echtheitseigenschaften die gleichen vorzüglichen sind wie die des Farbstoffs von Beispiel I.solves. Its solution in concentrated sulfuric acid is orange-red. He dyes on wool in acidic bath a yellow tan; the dye baths are well exhausted. When re-chrome plating the result is a yellow-tinged deep brown whose fastness properties are the same excellent are like that of the dye of Example I.
In analoger Weise lassen sich eine große Anzahl weiterer Kombinationen herstellen, von denen die wichtigsten in folgender Tabelle charakterisiert sind:A large number of other combinations can be produced in an analogous manner, the most important of which are characterized in the following table:
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