DE118655C - - Google Patents
Info
- Publication number
- DE118655C DE118655C DENDAT118655D DE118655DA DE118655C DE 118655 C DE118655 C DE 118655C DE NDAT118655 D DENDAT118655 D DE NDAT118655D DE 118655D A DE118655D A DE 118655DA DE 118655 C DE118655 C DE 118655C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- naphthylamine
- sulfonic acid
- blue
- diazo compounds
- 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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- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 15
- 239000000975 dye Substances 0.000 claims description 12
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 4
- HPNTZCAYLSSXRP-UHFFFAOYSA-N 4-phenylnaphthalen-1-amine Chemical compound C12=CC=CC=C2C(N)=CC=C1C1=CC=CC=C1 HPNTZCAYLSSXRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 102100008055 TUBB4A Human genes 0.000 description 2
- 101710034464 TUBB4A Proteins 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000001875 compounds Chemical class 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
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 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
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/053—Amino naphthalenes
- C09B31/057—Amino naphthalenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
KAISERLICHES jfk IMPERIAL jfk
PATENTAMT.PATENT OFFICE.
Es hat sich ergeben, dafs werthvolle blaue sekundäre Disazofarbstoffe von indigoähnlicher Nuance entstehen, wenn d-, a4-Phenylnaphtylaminsulfosäure, welche nach dem Verfahren des Patentes 70349 durch Erhitzen von O1 a4-Naphtylaminsulfosäure mit Anilin , und salzsaurem Anilin dargestellt werden kann, mit den Diazoverbindungen derjenigen Amidoazoproducte gekuppelt wird, die durch Einwirkung von Diazoverbindungen auf die sogen. Cleveschen A1 ß3- und Ct1 ß4-Naphtylaminsulfosäuren erhalten werden.It has been found that valuable blue secondary disazo dyes of indigo-like shade are formed when d-, a 4 -phenylnaphthylamine sulfonic acid, which can be prepared according to the method of patent 70349 by heating O 1 a 4 -naphthylamine sulfonic acid with aniline, and hydrochloric aniline, is coupled with the diazo compounds of those Amidoazoproducte, the so-called by the action of diazo compounds. Cleve's A 1 ß 3 - and Ct 1 ß 4 -naphtylamine sulfonic acids are obtained.
Diese Beobachtung ist deshalb bemerkenswerth, weil Farbstoffe von ähnlichem Typus, z.B. diejenigen des .Patentes 73901, durchweg schwarze Nuancen liefern.This observation is remarkable because dyes of a similar type, e.g. those of patent 73901, consistently deliver black nuances.
Das Verfahren ist das für die Darstellung derartiger Farbstoffe übliche.The procedure is that which is usual for the preparation of such dyes.
Der in üblicher Weise aus 9,3 kg Anilin und 24,5 kg Ci1 ß4-naphtylaminsulfosaurem Natrium hergestellte Amidoazokörper wird in 300 1 Wasser suspendirt und mit 7 kg Nitrit und 35 kg Salzsäure (20° B.) unter Kühlung versetzt. Nach etwa 12 stündigem Rühren ist die Diazotirung beendigt. Der abgeschiedene Diazokörper wird filtrirt, mit Wasser gewaschen und darauf mit 200 1 Wasser angeschlämmt in eine Lösung von 29,9 kg α.Ύ ci4-Phenylnaphtylaminsulfosäure und 35 kg essigsaurem Natrium in 500 1 Wasser eingetragen. Nach 12 stündigem Rühren wird auf ca. 60 ° angewärmt und mit Soda alkalisch gemacht. Der Farbstoff fällt dann krystallinisch aus.The amidoazo body prepared in the usual way from 9.3 kg of aniline and 24.5 kg of Ci 1 ß 4 -naphtylaminsulfosaurem sodium is suspended in 300 l of water and mixed with 7 kg of nitrite and 35 kg of hydrochloric acid (20 ° B.) with cooling. After about 12 hours of stirring, the diazotization is complete. The separated diazo body is filtered, washed with water and then slurried with 200 l of water in a solution of 29.9 kg of α. Ύ ci 4 -Phenylnaphtylamine sulfonic acid and 35 kg of sodium acetic acid entered in 500 l of water. After stirring for 12 hours, the mixture is warmed to approx. 60 ° and made alkaline with soda. The dye then precipitates in a crystalline manner.
Er färbt Wolle in essigsaurem Bade in schönen, klaren, blauen Nuancen an, welche alkaliecht und lichtecht sind und sich durch eine hervorragende Walkechtheit auszeichnen.He dyes wool in an acetic acid bath in beautiful, clear, blue shades, which are alkali-fast and lightfast and are characterized by excellent flexing fastness.
14,3 kg ß-Naphtylamin werden in üblicher Weise diazotirt und mit 24,5 kg Ci1 ß4-Naphtylaminsulfosäure gekuppelt. Der so erhaltene Amidoazokörper wird in 450 1 Wasser suspendirt und unter Kühlung mit 7 kg Nitrit und 35 kg Salzsäure (200B.) versetzt. Man läfst das Gemisch nun unter Umrühren bis zur Beendigung der Diazotirung (ca. 12 Stunden), stehen. Die ausgeschiedene Diazoverbindung wird filtrirt, durch Auswaschen von der überschüssigen Säure befreit und hierauf mit 300 1 Wasser angerührt. Die so erhaltene dünne Paste rührt man dann in eine Lösung von 29,9 kg Ct1 a4-Phenylnaphtylaminsulfosäure und 30 kg Natriumacetat in 600 1 Wasser bei gewöhnlicher Temperatur ein. Nach weiterem ca. 12 stündigem Rühren wird auf ca. 60 ° angewärmt und mit Soda alkalisch gemacht. Der unter Zusatz von Kochsalz ausgeschiedene Farbstoff wird filtrirt und getrocknet.14.3 kg of ß-naphthylamine are diazotized in the usual way and coupled with 24.5 kg of Ci 1 ß 4 -naphthylamine sulfonic acid. The Amidoazokörper thus obtained is suspended in 450 1 of water and while cooling with 7 kg of nitrite and 35 kg of hydrochloric acid (20 0 B.) was added. The mixture is then left to stand with stirring until the diazotization has ended (approx. 12 hours). The precipitated diazo compound is filtered, freed from the excess acid by washing, and then mixed with 300 liters of water. The thin paste thus obtained is then stirred into a solution of 29.9 kg of Ct 1 a 4 -phenylnaphthylamine sulfonic acid and 30 kg of sodium acetate in 600 l of water at ordinary temperature. After stirring for a further 12 hours, the mixture is warmed to approx. 60 ° and made alkaline with soda. The dye precipitated with the addition of common salt is filtered and dried.
Er färbt Wolle in essigsaurem Bade in etwas grünstichigeren Nuancen an als der in Bei-It stains wool in an acetic acid bath in slightly greener shades than that in both
spiel I beschriebene Farbstoff. Die Echtheitseigenschaften sind bei beiden Farbstoffen . die gleichen.game I described dye. The fastness properties are the same for both dyes. the same.
In analoger Weise, werden die anderen Farbstoffe dargestellt. Wir erwähnen beispielsweise die Producte, welche folgende Amine an ersterThe other dyes are represented in an analogous manner. We mention for example the products which the following amines come first
Stelle enthalten: a-Naphtylamin, p-Nitranilin, m - Amidobenzolsulfosäure, Amidosalicylsäure, ax a2-Naphtylaminsulfosäure, P1 ßs-Naphtylaminsulfosä'ure. Place contain: a-naphthylamine, p-nitraniline, m - amidobenzene sulfonic acid, amidosalicylic acid, a x a 2 -naphtylamine sulfonic acid, P 1 ß s -naphtylamine sulfonic acid.
In der folgenden Tabelle sind die Nuancen einer Anzahl der neuen Farbstoffe aufgeführt.The following table lists the nuances of a number of the new dyes.
55
55 55
55
55
55 55
55
5555
55
5. Amidosalicylsäure J
6. a-Naphtylamin■ . ' ■ - 4 · "4
5. Amidosalicylic Acid J.
6. α-Naphthylamine ■. '■ -
55
55 55
55
55
55
5555
55
55
8. Ci1 a2-Naphtylaminsulfosäure -7 · ß- 5, 4
8. Ci 1 a 2 -naphtylamine sulfonic acid -
55 55 ■ ■
55
grünstichig blau55
greenish blue
10. p-Nitranilin
11. Amidosalicylsäure ■
12. a-Naphtylamin9 ßl ß3 ~ 55
10. p-nitroaniline
11. Amidosalicylic acid ■
12. α-Naphthylamine
grünblau
blau
5555 55
green Blue
blue
55
14. Ct1 a2 -Naphtylaminsulfosäure -
16. p-Nitranilin13 · ß- 5, 4
14. Ct 1 a 2 -naphtylamine sulfonic acid -
16. p-nitroaniline
grünstichig blau
blau
grünblau.55
greenish blue
blue
green Blue.
- «ißt
- «1 ßt- «eat *
- «eats
- «1 ß
- «iß8 - «eat 8
- «eat 8
- «iß*
- «iß3
- «iß8 - «eats
- «eat *
- «eat 3
- «eat 8
- «! 03 - «1 ß *
- «! 0 3
Claims (1)
Die besonderen Ausführungsformen des Anspruchs 1 unter Verwendung der Diazoverbindungen folgender Amine an erster Stelle: Anilin, a-Naphtylamin, ß-Naphtylamin, p-Nitranilin, m-Amidobenzolsulfosäure, Amidosalicylsäure, ax a2-Naphfylaminsulfosäure, P1 ß3-Naphtylaminsulfosäure.sucked Cleve's a x ß 3 - and a x 0 4 -naphtylamine sulfonic acids are obtained.
The particular embodiments of claim 1 using the diazo compounds of the following amines in the first place: aniline, α-naphthylamine, β-naphthylamine, p-nitraniline, m-amidobenzenesulfonic acid, amidosalicylic acid, a x a 2 -naphthylamine sulfonic acid, P 1 ß 3 -naphthylamine sulfonic acid.
Publications (1)
Publication Number | Publication Date |
---|---|
DE118655C true DE118655C (en) |
Family
ID=387836
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT118655D Active DE118655C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE118655C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3483183A (en) * | 1965-08-20 | 1969-12-09 | Allied Chem | Process for isolating dry,water-soluble azo dyes |
-
0
- DE DENDAT118655D patent/DE118655C/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3483183A (en) * | 1965-08-20 | 1969-12-09 | Allied Chem | Process for isolating dry,water-soluble azo dyes |
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