DE239543C - - Google Patents
Info
- Publication number
- DE239543C DE239543C DENDAT239543D DE239543DA DE239543C DE 239543 C DE239543 C DE 239543C DE NDAT239543 D DENDAT239543 D DE NDAT239543D DE 239543D A DE239543D A DE 239543DA DE 239543 C DE239543 C DE 239543C
- Authority
- DE
- Germany
- Prior art keywords
- brown
- green
- amino
- anthraquinone
- gray
- 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
- FZEYVTFCMJSGMP-UHFFFAOYSA-N Acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000984 vat dye Substances 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 241000394591 Hybanthus Species 0.000 claims 1
- 240000000358 Viola adunca Species 0.000 claims 1
- 235000005811 Viola adunca Nutrition 0.000 claims 1
- 235000013487 Viola odorata Nutrition 0.000 claims 1
- 235000002254 Viola papilionacea Nutrition 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 240000007817 Olea europaea Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- AMWKTROIQUGOTA-UHFFFAOYSA-N 2-[(4-amino-9,10-dioxoanthracen-1-yl)amino]benzoic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC1=CC=CC=C1C(O)=O AMWKTROIQUGOTA-UHFFFAOYSA-N 0.000 description 1
- CGYGETOMCSJHJU-UHFFFAOYSA-N 2-chloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC=C21 CGYGETOMCSJHJU-UHFFFAOYSA-N 0.000 description 1
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N Bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 241000872198 Serjania polyphylla Species 0.000 description 1
- 241001284352 Terminalia buceras Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Landscapes
- Coloring (AREA)
- Cosmetics (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22 b. GRUPPECLASS 22 b. GROUP
FARBWERKE vorm. MEISTER LUCIUS & BRÜNING in HÖCHST a. M.FARBWERKE vorm. MASTER LUCIUS & BRÜNING in HÖCHST a. M.
Verfahren zur Darstellung von Küpenfarbstoffen der Anthrachinonreihe,Process for the preparation of vat dyes of the anthraquinone series,
Patentiert im Deutschen Reiche vom 2. November 1909 ab.Patented in the German Empire on November 2nd, 1909.
Es wurde gefunden, daß man wertvolleIt has been found to be valuable
Küpenfarbstoffe gewinnt durch Einführung von Radikalen, wie Alkyle, Aryle, Acyle oder Anthrachinonreste in 4 - Amino -1 · 2 - anthrachinonakridon. Vat dyes gained through the introduction of radicals such as alkyls, aryls, acyles or Anthraquinone residues in 4 - amino -1 · 2 - anthraquinone acridone.
ioTeile4-Amino-i · 2-anthrachinonakridon (erhältlich aus 4-Amino-i-anthrachinonylanthranilsäure z. B. durch Einwirkung von Chlorsulfonsäure), 10 Teile a - Chloranthrachinon, 1 Teil Kupferchlorür, 5 Teile wasserfreies Natriumacetat und 400 Teile Nitrobenzol werden 5 Stunden gekocht. Das Nitrobenzol wird durch Dampfdestillation entfernt. Das erhaltene Kondensationsprodukt ist ein schwarzes Pulver, das sich in konzentrierter Schwefelsäure mit olivgrüner Farbe löst. In alkalischem Hydrosulfit löst es sich mit rotbrauner Farbe und färbt Baumwolle grau bis tiefschwarz von hervorragender Echtheit. 10 parts of 4-amino-i · 2-anthraquinone acridone (obtainable from 4-amino-i-anthraquinonylanthranilic acid, e.g. by the action of chlorosulfonic acid), 10 parts of a -chloranthraquinone, 1 part of copper chloride, 5 parts of anhydrous sodium acetate and 400 parts of nitrobenzene take 5 hours cooked. The nitrobenzene is removed by steam distillation. The condensation product obtained is a black powder that dissolves in concentrated sulfuric acid with an olive green color. It dissolves in alkaline hydrosulphite with a red-brown color and dyes cotton gray to deep black with excellent fastness.
In analoger Weise werden andere Radikale in die Aminogruppe des 4-Amino-i · 2-anthrachinonakridons eingeführt.In an analogous manner, other radicals are converted into the amino group of the 4-amino-i · 2-anthraquinone acridone introduced.
Einige der so erhältlichen Farbstoffe sind in der folgenden Tabelle charakterisiert.Some of the dyes obtainable in this way are characterized in the following table.
der
Substanzcolour
the
substance
in konzentrierter
Schwefelsäure) Solution
in more concentrated
sulfuric acid
der '
Küpecolour
the '
Vat
auf
BaumwolleColoration
on
cotton
bis schwarzGray
to black
25 NH2
'+ α - ChloranthrachinonI.
25 NH 2
'+ α - chloranthraquinone
3030th
35 +β - Chloranthrachinon NH 2
35 + β - chloranthraquinone
Farbstoff ausDye off
Farbecolour
der Substanz Lösung
η konzentrierter
Schwefelsäurethe substance solution
η more concentrated
sulfuric acid
Farbecolour
derthe
KüpeVat
AusfärbungColoration
auf Baumwolleon cotton
HN-HN-
s/s /
c-1 c- 1
Il O Il O
BenzoylchloridBenzoyl chloride
HN-HN-
,c-, c-
Il O Il O
N H2 + Brombenzol NH 2 + bromobenzene
HN—, HN -,
(J~(J ~
Il O Il O
NFL1 -\- ρ - Dibrombenzol NFL 1 - \ - ρ - dibromobenzene
HN-HN-
/C-/ C-
IlIl
NH, ■ -{- a - Chlornaphtalin NH, ■ - {- a - chloronaphthalene
blau rotbraunblue red-brown
dunkelgrün braundark green brown
dunkelgrün graubraundark green gray brown
blau graubraunblue gray-brown
NHNH
dunkelgrün braundark green brown
β - Chlornaphtalinβ - chloronaphthalene
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE239543C true DE239543C (en) |
Family
ID=498976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT239543D Active DE239543C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE239543C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE940131C (en) * | 1943-12-28 | 1956-03-08 | Ciba Geigy | Process for the production of Kuepen dyes |
| DE946735C (en) * | 1951-01-09 | 1956-08-02 | Cassella Farbwerke Mainkur Ag | Process for the production of Kuepen dyes |
| DE967327C (en) * | 1943-12-28 | 1957-10-31 | Ciba Geigy | Process for the production of Kuepen dyes |
| DE1112800B (en) * | 1959-06-18 | 1961-08-17 | Basf Ag | Process for the preparation of Kuepen dyes of the 4-amino-anthraquinone-2, 1 (N) -1 ', 2' (N) -benzene-acridone series |
-
0
- DE DENDAT239543D patent/DE239543C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE940131C (en) * | 1943-12-28 | 1956-03-08 | Ciba Geigy | Process for the production of Kuepen dyes |
| DE967327C (en) * | 1943-12-28 | 1957-10-31 | Ciba Geigy | Process for the production of Kuepen dyes |
| DE946735C (en) * | 1951-01-09 | 1956-08-02 | Cassella Farbwerke Mainkur Ag | Process for the production of Kuepen dyes |
| DE1112800B (en) * | 1959-06-18 | 1961-08-17 | Basf Ag | Process for the preparation of Kuepen dyes of the 4-amino-anthraquinone-2, 1 (N) -1 ', 2' (N) -benzene-acridone series |
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