DE171904C - - Google Patents
Info
- Publication number
- DE171904C DE171904C DENDAT171904D DE171904DA DE171904C DE 171904 C DE171904 C DE 171904C DE NDAT171904 D DENDAT171904 D DE NDAT171904D DE 171904D A DE171904D A DE 171904DA DE 171904 C DE171904 C DE 171904C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dye
- parts
- wool
- diazotized
- 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
Links
- 210000002268 Wool Anatomy 0.000 claims description 6
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 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 claims 1
- 239000000975 dye Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-Nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 description 1
- ZIPJXJGTIGXUSE-UHFFFAOYSA-N 6-diazocyclohexa-2,4-dien-1-ol Chemical class OC1C=CC=CC1=[N+]=[N-] ZIPJXJGTIGXUSE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Blue Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N Picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229940114148 picric acid Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229950002929 trinitrophenol Drugs 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
PATENTAMT.PATENT OFFICE.
Kombiniert man diazotierte 6-Nitro-2-amidophenol-4-sulfosäure mit ß-Naphtol, so erhält man bekanntlich (vergl. Patentschrift 143892) einen Farbstoff, der Wolle in saurem Bade violett anfärbt und durch Chromieren in Schwarz übergeführt wird.Combine diazotized 6-nitro-2-amidophenol-4-sulfonic acid with ß-naphtol, as is known (see patent specification 143892), a dye is obtained, the wool in acidic Bath is colored purple and converted to black by chroming.
Bei Verwendung von ß-Oxynaphtoesäure Fp. 2i6° an Stelle von ß-Naphtol zum Aufbau eines analogen Farbstoffes konnte ähnliehe Nuance und Vermehrung des Beizencharakters erwartet werden. Merkwürdigerweise wirkt die Carboxylgruppe aber ungünstig auf die Beizfähigkeit; der Farbstoff wird beim Chromieren geschwächt. Ganz eigenartig ist jedoch der Einfluß der Carboxylgruppe auf die direkt erhaltene Nuance des neuen Farbstoffes: Statt eines Violett erhält man auf Wolle schon in 2prozentiger Ausfärbung ein Indigoblau, das wegen seinerWhen using ß-oxynaphtoic acid mp. 216 ° instead of ß-naphthol for the structure of an analogous dye could have a similar shade and increase in the character of the stain to be expected. Strangely enough, the carboxyl group has an unfavorable effect on the pickling ability; the coloring is weakened by chroming. However, the influence of the carboxyl group is quite peculiar on the directly obtained shade of the new dye: Instead of a violet, you get 2 percent strength on wool Coloring an indigo blue, because of its
ao grünstichigen Nuance und des lebhaften Überscheines von besonderem technischen Werte ist.ao greenish nuance and the lively excess of particularly technical Values is.
Eine solche Verschiebung der Nuance durch die Carboxylgruppe von Violett nach Blau konnte nicht vorausgesehen werden, zumal auch die wenigen in der Literatur beschriebenen Farbstoffe aus Diazophenolen und ß-Oxynaphtoesäure Fp. 216° ganz andere Nuancen aufweisen.Such a shift in shade through the carboxyl group from purple to Blue couldn't be foreseen, especially the few in literature described dyes from diazophenols and ß-oxynaphtoic acid mp. 216 ° completely different Have nuances.
Der in der Patentschrift 111330 beschriebene Farbstoff aus diazotierter Pikraminsäure und ß-Oxynaphtoesäure färbt Wolle in saurem Bade rötlichschwarz.The diazotized picric acid dye described in patent specification 111330 and ß-oxynaphthoic acid dyes wool in an acidic bath reddish black.
Die aus der diazotierten o-Nitranilin-p-sulfosäure darstellbare Diazophenolsulfosäure liefert bei Kombination mit ß-Oxynaphtoesäure einen Farbstoff, welcher Wolle in saurem Bade bläulichrot anfärbt (vergl. Patentschrift 138268). .The one from the diazotized o-nitroaniline-p-sulfonic acid Diazophenolsulfonic acid that can be represented is obtained when combined with ß-oxynaphthoic acid a dye which dyes wool bluish-red in an acidic bath (see patent specification 138268). .
Mit isomeren Nitroamidophenolsulfosäuren läßt sich ebenfalls ein gleicher Effekt nicht erzielen. So färbt z. B. der aus der 4-Nitro-2-amidophenol-6-sulfosäure dargestellte Farbstoff Wolle in saurem Bade trüber und schwärzlicher, .The same effect cannot be achieved with isomeric nitroamidophenol sulfonic acids either achieve. So z. B. that from 4-nitro-2-amidophenol-6-sulfonic acid depicted dye wool in an acid bath more cloudy and blacker,.
Das Verfahren sei an folgendem Beispiel erläutert:The procedure is explained using the following example:
64 Teile 6-nitro-2-amidophenol-4-sulfosaures Natron werden in Wasser gelöst und mit 11 ο Teilen Salzsäure 20 ° Be. und 17,5 Teilen Natriumnitrit bei etwa 10° diazotiert. Die Diazolösung läßt man einfließen in eine kalt gehaltene Lösung von 50 Teilen β-Oxy-. naphtoesäure Fp. 216 in 900 Teilen Wasser und 40 Teilen Natronlauge 35 ° Be., welcher noch 75 Teile Soda zugesetzt waren. Nach Vollendung der Kombination erwärmt man auf 70° und fällt den Farbstoff durch Zusatz von Salz und etwas Salzsäure.64 parts of 6-nitro-2-amidophenol-4-sulfonic acid sodium are dissolved in water and with 11 o parts hydrochloric acid 20 ° Be. and 17.5 parts Sodium nitrite diazotized at about 10 °. The diazo solution is allowed to flow into a cold held solution of 50 parts of β-oxy-. naphthoic acid m.p. 216 in 900 parts of water and 40 parts of sodium hydroxide solution 35 ° Be., to which 75 parts of soda were added. To When the combination is complete, the mixture is heated to 70 ° and the dye is precipitated by addition of salt and a little hydrochloric acid.
Er stellt nach dem Trocknen ein schwarzbraunes Pulver dar und löst sich in Wasser mit violetter, in konzentrierter Schwefelsäure mit bläulichroter Farbe. Die wässerigeAfter drying, it is a black-brown powder and dissolves in water with violet, in concentrated sulfuric acid with a bluish red color. The watery one
Lösung wird durch Zusatz von Salzsäure gelbrot,'durch Natronlauge bläulichrot.The solution becomes yellow-red with the addition of hydrochloric acid, and bluish-red with sodium hydroxide solution.
Der ■ neue Farbstoff besitzt außer der schönen Nuance noch die wertvolle Eigenschaft, baumwollene Effektfäden nicht anzufärben; er wird auch bei künstlicher Beleuchtung nicht verändert.In addition to the beautiful shade, the ■ new dye also has the valuable property not to dye cotton effect threads; it will also work with artificial lighting not changed.
Claims (1)
Verfahren zur Darstellung eines Wolle in saurem Bade blau färbenden Monoazofarbstoffes, darin bestehend, daß man diazotierte 6-Nitro-2-amidophenol-4-sulfosäure mit β-Oxynaphtoesäure Fp. 2160 kombiniert.Patent claim:
A method for displaying a wool in an acid bath bluing monoazo dye consisting in diazotized 6-nitro-2-amidophenol-4-sulfonic acid with β-oxynaphthoic acid, mp. 216 0 combined.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE171904C true DE171904C (en) |
Family
ID=436839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT171904D Active DE171904C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE171904C (en) |
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0
- DE DENDAT171904D patent/DE171904C/de active Active
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