DE116980C - - Google Patents
Info
- Publication number
- DE116980C DE116980C DENDAT116980D DE116980DA DE116980C DE 116980 C DE116980 C DE 116980C DE NDAT116980 D DENDAT116980 D DE NDAT116980D DE 116980D A DE116980D A DE 116980DA DE 116980 C DE116980 C DE 116980C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- red
- water
- naphthylamine
- dye
- 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
- 239000000975 dye Substances 0.000 claims description 9
- 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 claims description 8
- 229940114148 picric acid Drugs 0.000 claims description 8
- 229950002929 trinitrophenol Drugs 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 210000002268 Wool Anatomy 0.000 claims description 4
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 240000007817 Olea europaea Species 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000001808 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- QXYMVUZOGFVPGH-UHFFFAOYSA-N Picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 2
- -1 a-naphthylamine sulfonic acids Chemical class 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQUAPDZFXWRKMB-UHFFFAOYSA-N Diazodinitrophenol Chemical compound [O-][N+](=O)C1C[O-][N+](=O)CCC(=[N]=N)C1=O LQUAPDZFXWRKMB-UHFFFAOYSA-N 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N Parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001046 green dye Substances 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
-
- 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
- C09B45/34—Preparation from o-monohydroxy azo compounds having in the o'-position an atom or functional group other than hydroxyl, alkoxy, carboxyl, amino or keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Im Verfolg der Untersuchungen, die das Ziel hatten, egalisirende Monoazofarbstoffe für Wolle zu gewinnen und die schon zur Auffindung der werthvollen Combinationen der diazotirten Pikraminsäure mit S1 ai - Amidonaphtolsülfosäuren geführt hatten, hat sich ergeben, dafs die diazotirte Pikraminsäure auch mit ß-Naphtylaminsulfosäuren Farbstoffe liefert, die durch Behandlung mit Chromaten auf der Faser, in olivgrünen Nuancen entwickelt, sich durch ihre Licht- und Alkaliechtheit sowie Wasserechtheit auszeichnen.In the course of the investigations which had the aim of obtaining leveling monoazo dyes for wool and which had already led to the discovery of valuable combinations of diazotized picric acid with S 1 a i -amidonaphthol sulfonic acids, it was found that diazotized picric acid also with β-naphthylamine sulfos Provides dyes that develop olive green nuances through treatment with chromates on the fiber, are characterized by their light and alkali fastness as well as water fastness.
Bei analoger Behandlung der aus Pikraminsäure und a-Naphtylaminsulfosäuren entstehenden Combinationen, deren eine schon in der englischen Patentschrift 21437 vom Jahre 1896 erwähnt ist, entstehen braune Färbungen, während die mit ß-Naphtylaminsulfosäuren darstellbaren olivgrün sind.With an analogous treatment of those formed from picric acid and a-naphthylamine sulfonic acids Combinations, one of which is already described in English patent specification 21437 from 1896 is mentioned, brown colorations arise, while those that can be displayed with ß-naphthylamine sulfonic acids are olive green.
j. Pikraminsäure -+- ßj a3-Naphtylaminsulfosäure. ,j. Picramic acid - + - βj a 3 -naphtylamine sulfonic acid. ,
22,5 kg ßj Ct8-Naphtylaminsulfosäure werden in 20 kg Soda und 500 1 Wasser gelöst und hierzu Diazodinitrophenol, bereitet in gewöhnlicher Weise aus 19,9 kg Pikrammsäure, hinzugegeben. Die Kuppelung ist in wenig Stunden beendet; man kocht auf, filtrirt und fällt mit Kochsalz. Der Farbstoff stellt ein ziegelrothes Pulver dar, welches sich in Wasser mit gelbrother, in alkalischem Wasser mit gelbrother, in cone. Schwefelsäure mit rother Farbe löst. Er färbt Wolle in saurem Bade bräunlich roth; diese Färbung geht bei Nachbehandeln mit Bichromat in ein wasch-, walk- und lichtechtes Olivgrün über.22.5 kg of ßj Ct 8 -naphtylamine sulfonic acid are dissolved in 20 kg of soda and 500 l of water and diazodinitrophenol, prepared in the usual way from 19.9 kg of picric acid, is added. The coupling is completed in a few hours; it is boiled, filtered and precipitated with table salt. The dye is a brick-red powder, which is mixed in water with yellow-red, in alkaline water with yellow-red, in cone. Dissolves sulfuric acid with a red color. He dyes wool brownish red in an acid bath; this color changes to a wash, mill and lightfast olive green when treated with bichromate.
2. Pikraminsäure -f- P1 ß3- und ßx ß4-2. Picramic acid -f- P 1 ß 3 - and ß x ß 4 -
Naphtylamin sulfosäure. '
Die aus 19,9 kg Pikraminsäure in gewohnter Weise hergestellte Diazoverbindüng giebt man
zu einer Lösung von 22,5 kg techn. JSS1 ß3- und
ßj ß4-Naphtylaminsulfosäure in 20 kg Soda und
500 1 Wasser. Der Farbstoff bildet sich sehr schnell und in wenigen Stunden ist die Kuppelung
beendet. Dann kocht man auf, filtrirt und salzt mit Kochsalz aus. Der Farbstoff stellt in trockenem Zustand ein rothbraunes
Pulver dar, welches sich in Wasser mit weinrother, in alkalischem Wasser mit rother, in
cone. Schwefelsäure mit gelbrother Farbe löst. Er färbt in saurem Bade gelbbraun. Beim
Nachbehandeln mit Bichromat geht die Färbung in ein schönes Oliv über von guter Wasch-,
Walk- und Lichtechtheit.Naphthylamine sulfonic acid. '
The diazo compound prepared in the usual way from 19.9 kg of picric acid is added to a solution of 22.5 kg of technical grade. JSS 1 ß 3 - and ßj ß 4 -naphtylamine sulfonic acid in 20 kg of soda and 500 l of water. The dye forms very quickly and the coupling is completed in a few hours. Then it is boiled, filtered and salted out with table salt. When dry, the dye is a red-brown powder, which is red in water in water, red in alkaline water, in cone. Sulfuric acid dissolves with a yellowish-red color. It turns yellow-brown in an acidic bath. When treated with bichromate, the color changes into a beautiful olive with good wash, milled and lightfastness.
3. Pikraminsäure + ß1ß2ß3-Naph-3. picric acid + ß 1 ß 2 ß 3 -Naph-
tylamindisulfosäure R.tylamine disulfonic acid R.
31 kg ßj ß2 ß8 - Naphtylamindisulfosäure R, gelöst in 23 kg Soda und 500 1 Wasser, werden unter Rühren mit der aus 19,9 kg Pikraminsäure in gewöhnlicher Weise hergestellten Diazo-31 kg ßj ß 2 ß 8 - naphthylamine disulfonic acid R, dissolved in 23 kg soda and 500 l water, are stirred with the diazo-acid prepared in the usual way from 19.9 kg picric acid
verbindung versetzt. Kuppelung tritt sofort ein und ist in kurzer Zeit beendet. Nach dem Aufkochen und Filtriren salzt man den Farbstoff mit Kochsalz aus. Dieser stellt in trockener Form ein dunkelbraunes Pulver dar, welches sich in Wasser mit rother, in alkalischem Wasser mit rother, in cone. Schwefelsäure mit blä'ulichrother Farbe löst.connection shifted. Coupling occurs immediately and is completed in a short time. After boiling and filtration, the dye is salted out with table salt. This puts in drier Form a dark brown powder, which is red in water, in alkaline Water with rother, in cone. Sulfuric acid with a bluish-red color dissolves.
Der Farbstoff färbt Wolle in saurem Bade in rothen Tönen an, welche beim Nachbehandeln mit Bichromat in wasch- und lichtechte olivgrüne Farbstoffe verwandelt werden.The dye stains wool in an acidic bath in red tones, which when it is aftertreated can be transformed into washable and lightfast olive green dyes with bichromate.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE116980C true DE116980C (en) |
Family
ID=386281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT116980D Active DE116980C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE116980C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416816A (en) * | 1972-06-28 | 1983-11-22 | Sandoz Ltd. | 1:2 Chromium complex of 1-amino-2-(3',5'-dinitro-2'-hydroxyphenylazo)-4-sulfonaphthalene and alkali metal salts thereof |
-
0
- DE DENDAT116980D patent/DE116980C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416816A (en) * | 1972-06-28 | 1983-11-22 | Sandoz Ltd. | 1:2 Chromium complex of 1-amino-2-(3',5'-dinitro-2'-hydroxyphenylazo)-4-sulfonaphthalene and alkali metal salts thereof |
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