DE220581C - - Google Patents
Info
- Publication number
- DE220581C DE220581C DENDAT220581D DE220581DA DE220581C DE 220581 C DE220581 C DE 220581C DE NDAT220581 D DENDAT220581 D DE NDAT220581D DE 220581D A DE220581D A DE 220581DA DE 220581 C DE220581 C DE 220581C
- Authority
- DE
- Germany
- Prior art keywords
- chloroanthraquinone
- benzoylamino
- purple
- brown
- aminoanthraquinone
- 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
- 238000000034 method Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims 1
- -1 anthraquinone imides Chemical class 0.000 claims 1
- 238000004048 vat dyeing Methods 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 3
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 3
- 244000061775 Olea africana Species 0.000 description 3
- 235000002852 Olea africana Nutrition 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC1=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=C1 WITKIIIPSSFHST-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UMHSKYSHOIGDPE-UHFFFAOYSA-N pyridine;quinoline Chemical compound C1=CC=NC=C1.N1=CC=CC2=CC=CC=C21 UMHSKYSHOIGDPE-UHFFFAOYSA-N 0.000 description 2
- KXMLYSJUXIUOHI-UHFFFAOYSA-N 1-amino-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2N KXMLYSJUXIUOHI-UHFFFAOYSA-N 0.000 description 1
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001809 detectable Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
- 239000000984 vat 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
.— JVl 220581 -KLASSE 22 b. GRUPPE .— JVl 220581 - CLASS 22 b. GROUP
Patentiert im Deutschen Reiche vom 17. April 1909 ab. Längste Dauer: 29. Oktober 1918.Patented in the German Empire on April 17, 1909. Longest duration: October 29, 1918.
Es wurde gefunden, daß man zu küpenfärbenden Derivaten des Anthrimids gelangt, wenn man im Verfahren des Patents 162824 solche Komponenten anwendet, welche außer den für die Kondensation erforderlichen Halogenbzw. Aminogruppen noch benzoylierte Aminreste enthalten. Dieses Ergebnis war überraschend, da hier Küpenfarbstoffe auch dann erhalten werden, wenn das zugrunde liegende Anthrimid keine küpenfärbende Eigenschaft besitzt, wie es z.B. bei dem α - α - Anthrimid der Fall ist.It has been found that vat-coloring derivatives of anthrimide are obtained, if one uses in the process of the patent 162824 such components, which except the halogen or necessary for the condensation. Amino groups or benzoylated amine residues contain. This result was surprising, since vat dyes are obtained here even if the underlying Anthrimide does not have any vat-coloring properties, as is the case with α - α - anthrimide, for example the case is.
3 Teile Monobenzoyl-i · 4-diaminoanthrachinon (erhalten durch Reduktion von i-Benzoyl-3 parts of monobenzoyl-i · 4-diaminoanthraquinone (obtained by reducing i-benzoyl-
20 Dye off
20th
in Pyridin
(Chinolin)solution
in pyridine
(Quinoline)
in konzentrierter
Schwefelsäuresolution
in more concentrated
sulfuric acid
auf
BaumwolleColoring,
on
cotton
+ 2-Chloranthrachinon oder
i-Benzoylamino-4-chloranthrachinon
25 + 2-Aminoanthrachinoni-Benzoylamino-4-aminoanthraquinone
+ 2-chloroanthraquinone or
i-Benzoylamino-4-chloroanthraquinone
25 + 2-aminoanthraquinone
+ i-Aminoanthrachinonι -Benzoylamino-4-chloroanthraquinone
+ i-aminoanthraquinone
i-Benzoylamino-5-aminoanthrachinon
-j- 2-Chloranthrachinon 30th
i-Benzoylamino-5-aminoanthraquinone
-j- 2-chloroanthraquinone
amino-4-nitroanthrachinon), 2 Teile 2-Chloranthrachinon, 3 Teile entwässertes Natriumacetat werden mit 30 Teilen Nitrobenzol unter Zusatz von 0,1 Teil Kupferchlorid gekocht, bis unangegriffene Ausgangsmaterialien in erheblicher Menge nicht mehr nachweisbar sind. Das durch Verdünnung mit geeigneten Mitteln wie Alkohol, Benzol oder durch Abtreiben des Nitrobenzols mit Wasserdampf isolierte Produkt wird abgesaugt und ausgewaschen.amino-4-nitroanthraquinone), 2 parts of 2-chloroanthraquinone, 3 parts of dehydrated sodium acetate are boiled with 30 parts of nitrobenzene with the addition of 0.1 part of copper chloride, until unaffected raw materials are no longer detectable in significant quantities. This can be done by diluting with suitable agents such as alcohol, benzene or by stripping off the Product isolated from nitrobenzene with steam is filtered off with suction and washed out.
Die Eigenschaften dieses Produkts, das man auch durch Kondensation von i-Benzoylamino-4-chloranthrachinon mit 2-Aminoanthrachinon erhält sowie einiger weiterer nach demselben Verfahren hergestellter Farbstoffe sind in folgender Tabelle zusammengestellt:The properties of this product can also be obtained from the condensation of i-benzoylamino-4-chloroanthraquinone obtained with 2-aminoanthraquinone and some other dyes prepared by the same process are in the following Table compiled:
5050
5555
6060
inonmixture
inon
in Pyridin
(Chinolin)solution
in pyridine
(Quinoline)
in konzentrierter
Schwefelsäuresolution
in more concentrated
sulfuric acid
auf
Baumwollecoloring
on
cotton
i-Benzoylamino-6-chlor-
anthrachinon
i-Benzoylamino-7-chlor-
anthrachinon
+ i-Aminoanthrach
10 5
i-Benzoylamino-6-chloro
anthraquinone
i-Benzoylamino-7-chloro-
anthraquinone
+ i-aminoanthrach
10
• + ι · 5-Diaminoanthrachinoni-Benzoylamino-4-chloroanthraquinone
• + ι · 5-diaminoanthraquinone
anthracbinon + 2-ChloranthrachinonDibenzoyl-i · 5-diamino-4 ■ 8-diamino-
anthracbinone + 2-chloroanthraquinone
Küpe: ) violett
warme j violett-
Küpe:) graucold) gray
Vat :) purple
warm j purple
Vat :) gray
+ 2-Aminoanthrachinon2o dibenzoyl-i · s-diamino ^ -chloranthraquinone
+ 2-aminoanthraquinone
Eigenschaften der bisher noch nicht beschriebenen Benzoylverbindungen:Properties of the benzoyl compounds not yet described:
AussehenAppearance
Lösungsolution
in Pyridinin pyridine
in konzentrierter
Schwefelsäure '■>in more concentrated
Sulfuric acid
ι-Benzoylamino-6-chloranthrachinon (ι-Benzoylamino-6-chloroanthraquinone (
i-Benzoylamino-7-chloranthrachinon Ji-Benzoylamino-7-chloroanthraquinone J
gelbes
Kristallmehlyellow
Crystal flour
gelbyellow
orangeorange
ι t 5-Dibenzoyldiamino-4 · 8-diaminoanthrachinon ι t 5-dibenzoyldiamino-4 · 8-diaminoanthraquinone
dunkelviolette
Nadelndark purple
Needles
blaublue
gelbyellow
ι · s-Dibenzoyldiamino^-chloranthrachinonι · s-Dibenzoyldiamino ^ -chloranthraquinone
braunrote Prismenbrown-red prisms
mit
grünem Schimmerwith
green shimmer
goldgelbgolden yellow
braunolivebrown olive
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE220581C true DE220581C (en) |
Family
ID=481620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT220581D Active DE220581C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE220581C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12084319B2 (en) | 2019-04-03 | 2024-09-10 | Liebherr-Werk Biberach Gmbh | Method and device for controlling a materials handling and/or construction machine |
-
0
- DE DENDAT220581D patent/DE220581C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12084319B2 (en) | 2019-04-03 | 2024-09-10 | Liebherr-Werk Biberach Gmbh | Method and device for controlling a materials handling and/or construction machine |
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