DE132644C - - Google Patents
Info
- Publication number
- DE132644C DE132644C DENDAT132644D DE132644DA DE132644C DE 132644 C DE132644 C DE 132644C DE NDAT132644 D DENDAT132644 D DE NDAT132644D DE 132644D A DE132644D A DE 132644DA DE 132644 C DE132644 C DE 132644C
- Authority
- DE
- Germany
- Prior art keywords
- violet
- blue
- amidophenol
- well
- heated
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- -1 aromatic nitro compounds Chemical class 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 240000000358 Viola adunca Species 0.000 description 5
- 235000005811 Viola adunca Nutrition 0.000 description 5
- 235000013487 Viola odorata Nutrition 0.000 description 5
- 235000002254 Viola papilionacea Nutrition 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 4
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 229940114148 picric acid Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229950002929 trinitrophenol Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- C09B49/00—Sulfur dyes
- C09B49/06—Sulfur dyes from azines, oxazines, thiazines or thiazoles
-
- 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
- C09B17/00—Azine dyes
- C09B17/02—Azine dyes of the benzene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Aus aromatischen Monaminen entstehen bekanntlich beim Erhitzen mit Nitrokörpern und einem Condensationsmittel wasserunlösliche gefärbte, chemisch nicht näher definirte Condensationsprodukte, welche als Nigrosine bezeichnet werden (vergl. z. B. Nietzki, organische Farbstoffe, i. Aufl., S. 146). Unter Anwendung von Diaminen ist es gelungen, wasserlösliche, amidirte Derivate herzustellen (vergl. z. B. die Patentschrift 44406).It is known that aromatic monamines are formed when heated with nitro bodies and colored condensation products which are insoluble in water with a condensation agent and are not chemically defined, which are called nigrosine (see e.g. Nietzki, organic dyes, i. Ed., P. 146). With the use of diamines we have succeeded in producing water-soluble, amidated To prepare derivatives (see, for example, patent specification 44406).
Es wurde nun gefunden, dafs unter Anwendung hydroxylirter aromatischer Amine neue Condensationsprodukte entstehen, welche sich von den bekannten dadurch unterscheiden, dafs sie alkalilöslich sind, also'intakte Hydroxylgruppen enthalten. Sie entstehen unter Abspaltung von Ammoniak, sind ebenfalls gefärbt und technisch besonders dadurch bedeutungsvoll, dafs sie bei der Schwefelschmelze, wie in der Patentschrift 117073 gezeigt ist, in neue schwefelhaltige Farbstoffe übergehen.It has now been found that using hydroxylated aromatic amines new condensation products arise, which differ from the known ones in that that they are soluble in alkali, i.e. contain intact hydroxyl groups. They are created by splitting off of ammonia, are also colored and technically particularly meaningful because that they are transformed into new ones in the sulfur melt, as shown in patent specification 117073 Sulfur-containing dyes pass over.
Das Verfahren zur Darstellung dieser neuen Condensationsprodukte, die als Hydroxylhaltige Nigrosine bezeichnet werden sollen, ist das allgemein für solche Farbstoffe übliche. Man erhitzt p-Amidophenol mit einem aromatischen Nitrokörper und einem Condensationsmittel bis zum Maximum der Farbstoffbildung. Die Mengenverhältnisse der angewendeten Ingredienzien können auch bei dem vorliegenden Verfahren schwanken. Im Allgemeinen ist jedoch die Wirkung der Polynitrokörper eine energischere, so dafs man hier mit einer kleineren Menge auskommt als unter Anwendung eines Mononitrokörpers.The process for the preparation of these new condensation products, which are called hydroxyl-containing Nigrosine are to be referred to, is the general common practice for such dyes. Man heats p-amidophenol with an aromatic nitro body and a condensing agent up to to the maximum of dye formation. The proportions of the ingredients used may also vary with the present method. Generally however the action of the polynitro bodies is more energetic, so that here one can manage with a smaller amount than with application of a mononitro body.
1. Ein Gemenge von 10 kg p-Amidophenol mit 5 kg salzsauren p-Amidophenol und 6 kg o-Nitrophenol wird langsam bis zum Eintreten der lebhaften Reaktion (bei ca. 145°) erhitzt; sobald diese nachgelassen hat, erhitzt man noch einige Stunden auf 160 bis 1700. Man erhält eine nach dem Erkalten harte, metallglänzende Schmelze, welche durch Auflösen in verdünnter Natronlauge und Ausfällen mit Salzsäure aufgearbeitet werden kann.1. A mixture of 10 kg of p-amidophenol with 5 kg of hydrochloric acid p-amidophenol and 6 kg of o-nitrophenol is slowly heated until the vigorous reaction occurs (at approx. 145 °); once this has subsided, the mixture is heated for a few hours at 160 to 170 0th After cooling, a hard, shiny metal melt is obtained which can be worked up by dissolving it in dilute sodium hydroxide solution and precipitating it with hydrochloric acid.
2. 11 kg p-Amidophenol, 15 kg salzsaures p-Amidophenol und 12 kg Nitrobenzol werden zusammen gemischt und im Laufe von 7 Stunden langsam von 140 bis i8o° bis zur Be endigung der Farbstoffbildung erhitzt.2. 11 kg of p-amidophenol, 15 kg of hydrochloric acid p-Amidophenol and 12 kg of nitrobenzene are mixed together and over the course of 7 hours slowly from 140 to 180 degrees to the Be the end of the dye formation heated.
3. Man ersetzt in dem vorigen Ansatz das Nitrobenzol durch 16 kg p-Nitranilin und erhitzt 6. Stunden lang von 130 bis 1700.In the previous approach 3. It replaces the nitrobenzene via 16 kg of p-nitroaniline and heated 6 hours from 130 to 170 0th
4. Ein Gemenge von 16,5 kg p-Amidophenol, 22 kg salzsaurem p-Amidophenol und 7 kg Dinitrophenol (OH: NO2: NO2 =1:2:4; wird im Laufe von 2 Stunden von 125 bis 2000 erhitzt. Die erhaltene Schmelze zeigt ebenfalls einen Metallglanz. An Stelle von Dinitrophenol kann man auch Pikrinsäure verwenden.4. A mixture of 16.5 kg of p-amidophenol, 22 kg of salt-acid p-amidophenol and 7 kg dinitrophenol (OH: NO 2: NO 2 = 1: 2: 4; is heated in the course of 2 hours, 125 to 200 0 The melt obtained also has a metallic luster. Picric acid can also be used instead of dinitrophenol.
Charakteristikder erhaltenen Produkte.Characteristics of the products obtained.
phenol undProduct of p-amido-
phenol and
Schwefelsäure
löslichin con.
sulfuric acid
soluble
dünnen mit
Wasserat Ver
thin with
water
löslichin caustic soda
soluble
Lösung mit
Zinkstaubalkaline
Solution with
Zinc dust
alkoholischen
LösungColor of
alcoholic
solution
(Beispiel i)o-nitrophenol
(Example i)
schlagblue down
blow
kehrt an der
Luft zurückdiscolored; colour
returns to the
Air back
(Beispiel 2)Nitrobenzene
(Example 2)
(Beispiel 3)ρ - nitroaniline
(Example 3)
(Beispiel 4)Dinitrophenol
(Example 4)
violettdirty
violet
blauviolettdirty
blue-violet
mit H Cl blau
violett.dirty purple
with H Cl blue
violet.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE132644C true DE132644C (en) |
Family
ID=400896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT132644D Active DE132644C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE132644C (en) |
-
0
- DE DENDAT132644D patent/DE132644C/de active Active
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