CH211040A - Process for the production of a nitrogen-containing condensation product. - Google Patents
Process for the production of a nitrogen-containing condensation product.Info
- Publication number
- CH211040A CH211040A CH211040DA CH211040A CH 211040 A CH211040 A CH 211040A CH 211040D A CH211040D A CH 211040DA CH 211040 A CH211040 A CH 211040A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrogen
- production
- condensation product
- brown
- containing condensation
- Prior art date
Links
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 4
- 239000007859 condensation product Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 244000061775 Olea africana Species 0.000 claims description 2
- 235000002852 Olea africana Nutrition 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- QZKRKMRVWWGTRU-UHFFFAOYSA-N 1,3-dichloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C)=C(Cl)C=C3C(=O)C2=C1 QZKRKMRVWWGTRU-UHFFFAOYSA-N 0.000 description 2
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 208544. Verfahren zur Herstellung eines stickstoffhaltigen Kondensationsproduktes. Es wurde gefunden, dass man ein stick- stoffhaltiges herstel len kann, wenn man 1 Mol 1,3-Dihalegen-2- methylanthrachinon mit 2 Mal 1-Amino-5- benzoylaminoanthrachinon umsetzt. Der neue Farbstoff ist ein,dunkelbraunes Pulver,
das sich in Schwefelsäure mit braunoliver Farbe löst und Baumwolle aus brauner Küpe in echten braunen Farbtönen färbt.
Als 1,3-Dihalogen-2-methylanthrachinon kann beispielsweise 1,3-Dichlor-2-methyl- anthrachinon verwendet werden.
Die Umsetzung mit 1-Amino:-5-benzoyl- aminoanthrachinon erfolgt zweckmässig in Gegenwart von Lösungs- oder Verteilungs- mitteln, z. B. Nitrobenzol, Dichlarbenzol oder Naphthalin und in Gegenwart von Katalysa toren, wie Kupfer oder Kupferverbindungen, sowie vorzugsweise in Anwesenheit von säurebindenden Mitteln, wie Natriumacetat und Alkalicarbonat, bei höherer Temperatur.
Beispiel: 14,5 Teile 1,3-Dichlor-2-methylanthra- ehinon, 34,5 Teile 1-Amino 5-benzoylamino- anthrachinon, 40 Teile wasserfreies Natrium carbonat, 1 Teil Kupferacetat und 300 Teile Naphthalin werden 18 Stunden zum Sieden erhitzt.
Das Reaktionsgemisch wird noch heiss mit 300 Teilen Chlorbenzol verdünnt und bei 90-100 filtriert. Der Rückstand wird mit Chlorbenzol sowie mit Alkohol ge waschen, mit Wasser ausgekocht, filtriert und getrocknet.
Additional patent to main patent No. 208544. Process for the production of a nitrogen-containing condensation product. It has been found that a nitrogen-containing one can be produced if 1 mole of 1,3-dihalogen-2-methylanthraquinone is reacted with 2 times 1-amino-5-benzoylaminoanthraquinone. The new dye is a dark brown powder
which dissolves in sulfuric acid with a brown-olive color and dyes cotton from a brown vat in real brown shades.
1,3-dichloro-2-methyl-anthraquinone, for example, can be used as 1,3-dihalo-2-methylanthraquinone.
The reaction with 1-amino: -5-benzoylaminoanthraquinone is expediently carried out in the presence of solvents or distributing agents, e.g. B. nitrobenzene, dichlorobenzene or naphthalene and in the presence of cata factors, such as copper or copper compounds, and preferably in the presence of acid-binding agents such as sodium acetate and alkali metal carbonate, at a higher temperature.
Example: 14.5 parts of 1,3-dichloro-2-methylanthraquinone, 34.5 parts of 1-amino 5-benzoylamino anthraquinone, 40 parts of anhydrous sodium carbonate, 1 part of copper acetate and 300 parts of naphthalene are heated to the boil for 18 hours .
The reaction mixture is diluted while still hot with 300 parts of chlorobenzene and filtered at 90-100. The residue is washed with chlorobenzene and with alcohol, boiled with water, filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208544T | 1938-07-20 | ||
| CH211040T | 1938-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211040A true CH211040A (en) | 1940-08-15 |
Family
ID=25724555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211040D CH211040A (en) | 1938-07-20 | 1938-07-20 | Process for the production of a nitrogen-containing condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211040A (en) |
-
1938
- 1938-07-20 CH CH211040D patent/CH211040A/en unknown
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