DE172168C - - Google Patents
Info
- Publication number
- DE172168C DE172168C DENDAT172168D DE172168DA DE172168C DE 172168 C DE172168 C DE 172168C DE NDAT172168 D DENDAT172168 D DE NDAT172168D DE 172168D A DE172168D A DE 172168DA DE 172168 C DE172168 C DE 172168C
- Authority
- DE
- Germany
- Prior art keywords
- black
- disulfonic acid
- dioxynaphthalene
- blue
- phenylenediamine
- 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
- 239000002253 acid Substances 0.000 claims description 17
- 239000000975 dye Substances 0.000 claims description 11
- 210000002268 Wool Anatomy 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 2
- 230000001808 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- JHZHQAKIEKBDQA-UHFFFAOYSA-N [N+](=O)([O-])CC(=O)NC1=CC=C(C=C1)N Chemical compound [N+](=O)([O-])CC(=O)NC1=CC=C(C=C1)N JHZHQAKIEKBDQA-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- JMGOORYWTOXUQE-XOBOFAKPSA-N (6Z)-4-amino-3-[(4-nitrophenyl)diazenyl]-5-oxo-6-(phenylhydrazinylidene)naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=2C=C(S(O)(=O)=O)\C(=N/NC=3C=CC=CC=3)C(=O)C=2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 JMGOORYWTOXUQE-XOBOFAKPSA-N 0.000 description 1
- ISFYBUAVOZFROB-UHFFFAOYSA-N 4-ethoxy-2-nitroaniline Chemical compound CCOC1=CC=C(N)C([N+]([O-])=O)=C1 ISFYBUAVOZFROB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N N-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 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 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß man durch Kuppeln der Diazoverbindungen des Nitroacetylp-phenylendiamins der folgenden Formel:It has been found that by coupling the diazo compounds of nitroacetylp-phenylenediamine of the following formula:
N ΗN Η
Ν Hn Ν H n
CH3-CO·CH 3 -CO
mit ι · 8 - Dioxynaphtalin -3*6- disulfosäure und nachfolgender Abspaltung der Acetylgruppe einen Monoazofarbstoffe erhält, welcher Wolle in saurem Bade blauschwarz färbt; außerdem zeichnet sich der Farbstoff besonders durch ein gutes Egalisierungsvermögen aus. Diese Eigenschaften waren nicht zu erwarten, da bekanntlich einerseits das nicht nitrierte Acetyl-p-phenylendiamin beim Kuppeln mit ι · 8 - Dioxynaphtalin - 3 · 6 - disulfosäure und Abspalten der Acetylgruppe ein Violett liefert (vergl. Patentschrift 73321) und andererseits aus der Patentschrift 80851 für das der hier verwendeten Nitroverbindung in seiner Konstitution nahestehende m-Nitrop-phenetidin bekannt war, daß es beim Kuppein mit der 1 · 8-Dioxynaphtalin-3 * 6-disulf osäure nicht etwa ein Schwarz, sondern ein Violettrot liefert. Es hat sich ferner gezeigt, daß auch dann, wenn man das Nitroacetylp-phenylendiamin statt mit der i.«8-Dioxynaphtalin-3 · 6-disulfosäure mit anderen Dioxynaphtalindisulfosäuren oder mit Amidonaphtoldisulfosäuren ■ kuppelt, man gleichfalls wertvolle, schwarze sauerfärbende Wollfarbstoffe erhält.with ι · 8 - dioxynaphthalene -3 * 6- disulfonic acid and subsequent cleavage of the acetyl group gives a monoazo dye, which Dyes wool blue-black in an acid bath; in addition, the dye is particularly notable characterized by a good leveling ability. These properties were not to be expected As is well known, on the one hand, the non-nitrated acetyl-p-phenylenediamine during coupling with ι · 8 - dioxynaphthalene - 3 · 6 - disulfonic acid and cleavage of the acetyl group gives a violet (see patent specification 73321) and on the other hand from patent specification 80851 for that of the nitro compound used here m-Nitrop-phenetidine, which is closely related in its constitution, was known to be found in the cupola with the 1 · 8-dioxynaphthalene-3 * 6-disulfonic acid not a black, but a Purple red supplies. It has also been shown that even if you use the nitroacetylp-phenylenediamine instead of the i. «8-dioxynaphthalene-3 · 6-disulfonic acid with other dioxynaphthalene disulfonic acids or with amidonaphthol disulfonic acids, one likewise Preserves valuable, black, acid-dyeing wool dyes.
Das neue Verfahren wird erläutert durch folgendesThe new method is illustrated by the following
19,5 Teile Mononitroacet-p-phenylendiamin (NH2: NO^: NH- CO-CH3= 1:2 : a) 19.5 parts mononitroacet-p-phenylenediamine (NH 2 : NO ^: NH- CO-CH 3 = 1: 2 : a)
werden in der bekannten Weise diazotiert und die so erhaltene Diazoverbindung in eine wässerige Lösung von 32 Teilen 1 · 8-Dioxynaphtalin-3 · 6-disulfosäure eingegossen. Nach kurzem Rühren wird etwas essigsaures Natron oder Soda zugesetzt, die Kupplung zu Ende geführt und der so entstandene Azofarbstoff ausgesalzen, abfiltriert und getrocknet. Er färbt Wolle rotviolett. Zur Abspaltung der Acetylgruppe wird der Farbstoff mit 8 Teilen 50 prozentiger Schwefelsäure gekocht, wobei sich das entacetylierte Produkt kristallinisch ausscheidet. Der so entstandene neue Farbstoff färbt Wolle in lebhaften blauschwarzen Nuancen an.are diazotized in the known manner and the diazo compound thus obtained in a aqueous solution of 32 parts of 1x8-dioxynaphthalene-3 · Poured 6-disulfonic acid. After stirring briefly, it will turn out to be a little bit of baking soda or soda was added, the coupling completed and the azo dye thus formed salted out, filtered off and dried. He dyes wool red-violet. To split off the Acetyl group, the dye is boiled with 8 parts of 50 percent sulfuric acid, whereby the deacetylated product separates out in crystalline form. The new dye created in this way colors wool in lively blue-black shades.
Die im Beispiel beschriebene Isolierung des acetylierten Farbstoffes kann auch unterbleiben. Nachdem die Kupplung beendet ist, kann man die Lösung desselben direkt mit verdünnter Schwefelsäure verkochen.The isolation of the acetylated dye described in the example can also be omitted. After the coupling has ended, the solution of the same can be boiled off directly with dilute sulfuric acid.
In der folgenden Tabelle sind die Färbeeigenschaften einer Anzahl der neuen Farbstoffe angegeben:The following table shows the coloring properties of a number of the new dyes specified:
Farbstoff aus Mononitroacet-p-phenylendiamin (nach der Kupplung r.. , w ,,Dye from mononitroacet-p-phenylenediamine (after coupling r .. , w ,,
entacetyliert) + lclrDt YVOUe deacetylated) + lclrDt YVOUe
ι · 8-Dioxynaphtalin-3 · 6-disulfosäure blauschwarzι · 8-Dioxynaphthalene-3 · 6-disulfonic acid blue-black
ι · 8-Dioxynaphtalin-2 · 4 - disulfosäure schwarzι · 8-Dioxynaphthalene-2 · 4-disulfonic acid black
ι · 5-Dioxynaphtalin-3 · 7-disulfosäure rotstichig blauschwarzι · 5-Dioxynaphthalene-3 · 7-disulfonic acid reddish blue-black
ι · 8- Amidonaphtol-3 · 6-disulfosäure (sauer gekuppelt) blauschwarzι · 8-amidonaphthol-3 · 6-disulfonic acid (acidic coupled) blue-black
ι · 8-Amidonaphtol-3 ' 6-disulfosäure (alkalisch gekupppelt) griinstichig blauschwarzι · 8-Amidonaphtol-3 '6-disulfonic acid (alkaline coupled) greenish bluish black
ι · 8- Amidonaphtol-4 · 6-disulfosäure (sauer gekuppelt) rotstichig blauschwarzι · 8- Amidonaphtol-4 · 6-disulfonic acid (acidic coupled) reddish blue-black
ι · 8-Amidonaphtol-4 · 6-disulfosäure (alkalisch gekuppelt) schwarzι · 8-Amidonaphtol-4 · 6-disulfonic acid (alkaline coupled) black
ι · 5-Amidonaphtol-2 · 7-disulfosäure (alkalisch gekuppelt) blauschwarzι · 5-Amidonaphtol-2 · 7-disulfonic acid (alkaline coupled) blue-black
2 · 8-Amidonaphtol-3 · 6-disulfosäure (alkalisch gekuppelt) blauschwarz.2 · 8-Amidonaphthol-3 · 6-disulfonic acid (alkaline coupled) blue-black.
Claims (1)
daß man die Diazoverbindungen des
Mononitroacet - ρ - phenylendiaminedyes for wool, consisting of
that the diazo compounds of
Mononitroacet - ρ - phenylenediamine
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE172168C true DE172168C (en) |
Family
ID=437080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT172168D Active DE172168C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE172168C (en) |
-
0
- DE DENDAT172168D patent/DE172168C/de active Active
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