DE611338C - Process for the production of halogen-containing Kuepen dyes - Google Patents
Process for the production of halogen-containing Kuepen dyesInfo
- Publication number
- DE611338C DE611338C DEI48204D DEI0048204D DE611338C DE 611338 C DE611338 C DE 611338C DE I48204 D DEI48204 D DE I48204D DE I0048204 D DEI0048204 D DE I0048204D DE 611338 C DE611338 C DE 611338C
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- production
- dyes
- kuepen dyes
- kuepen
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000975 dye Substances 0.000 title description 7
- 229910052736 halogen Inorganic materials 0.000 title description 3
- 150000002367 halogens Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000984 vat dye Substances 0.000 claims description 4
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 238000007792 addition Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- ROUBHWCHDZARQJ-UHFFFAOYSA-N 1-amino-2-(7-oxobenzo[a]phenalen-1-yl)anthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=CC=CC=C3C3=C2C1=CC=C3C1=C(N)C(C(=O)C2=CC=CC=C2C2=O)=C2C=C1 ROUBHWCHDZARQJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
- C09B5/40—Condensation products of benzanthronyl-amino-anthraquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung halogenhaltiger Küpenfarbstoffe In dem zweiten Zusatzpatent 61o 849 wird ein Verfahren zur Herstellung von halogenhaltigen Küpenfarbstoffen beschrieben, das darin besteht, daß man die Küpenfarbstoffe, welche gemäß Patent 52o 876 und dessen Zusatzpatenten 522 970, 525 945 und 541 267 erhalten werden und Acylaminogruppen -enthaltende. - Kondensationsprodukte aus Benzanthronyl-i-aminoanthrachinonen darstellen, gemäß dem Verfahren des Hauptpatents mit chlorierenden Mitteln unter milden Bedingungen behandelt. Gemäß dem Verfahren des ersten Zusatzpatents 6o8 795 werden die gleichen Ausgangskörper zunächst in hochchlorierte Derivate übergeführt und aus diesen durch Chlorwasserstoffabspaltung bzw. Enthalogenierung niedrigchlorierte Farbstoffe gewonnen.Process for the production of halogen-containing vat dyes In the second additional patent 61o 849 a process for the production of halogen-containing vat dyes is described, which consists in that the vat dyes which are obtained according to patent 52o 876 and its additional patents 522 97 0 , 525 945 and 541 267 and Acylamino groups -containing. - represent condensation products of benzanthronyl-i-aminoanthraquinones, treated according to the process of the main patent with chlorinating agents under mild conditions. According to the process of the first additional patent 6o8 795, the same starting bodies are first converted into highly chlorinated derivatives and dyes with low chlorine content are obtained from these by elimination of hydrogen chloride or dehalogenation.
Es wurde nun gefunden, daß man zu ähnlichen wertvollen Farbstoffen gelangt, welche im Vergleich zu den Ausgangskörpern ebenfalls durch eine nach blau verschobene Nuance und verbesserte Chlorechtheit der damit erzielten Färbungen ausgezeichnet sind, wenn man die obigen Ausgangskörper einer Bromierung unter milden Bedingungen unterwirft. Beispiel 25 kg des Farbstoffes, erhalten gemäß Patent 520 876, Beispiel i, werden in fein verteilter Form mit einer Lösung von 16 kg Brom in etwa Zoo kg Eisessig bei Gegenwart von 25 kg Natriumacetat und einer geringen Menge Jod versetzt, und die Mischung wird dann längere Zeit gerührt. Hierauf wird die Reaktionsmasse zum Kochen erhitzt und unter Rückflußkühlung noch etwa 3 Stunden gekocht. Nach Absaugen und Auswaschen wird ein Farbstoff erhalten, der ungefähr i i bis 12 % Brom enthält und der, aus Schwefelsäure gelöst, aus blauvioletter Küpe Baumwolle in echten olivfarbenen Tönen färbt, die wesentlich blauer sind als die des Ausgangsfarbstoffes. Bei starker Einwirkung von Chlorlauge auf -die Färbung ist eine gegenüber dem Ausgangsmaterial verbesserte Chlorechtheit festzustellen. Die Lösungsfarbe in konzentrierter Schwefelsäure ist grün.It has now been found that similar valuable dyes can be obtained which, in comparison to the original bodies, also goes through a to blue The shifted shade and improved chlorine fastness of the dyeings obtained therewith are excellent are, if one of the above starting bodies a bromination under mild conditions subject. Example 25 kg of the dye obtained according to patent 520,876, example i, are finely divided with a solution of 16 kg of bromine in about zoo kg Glacial acetic acid added in the presence of 25 kg of sodium acetate and a small amount of iodine, and the mixture is then stirred for a long time. The reaction mass then becomes heated to a boil and refluxed for about 3 hours. After suction and washing out a dye is obtained which contains about i i to 12% bromine and that, dissolved from sulfuric acid, from blue-violet cotton vat in real olive-colored Colors that are much bluer than that of the original dye. With strong Effect of chlorine lye on -the coloration is opposite to that of the starting material detect improved chlorine fastness. The solution paint in concentrated sulfuric acid is green.
Zu ähnlichen Farbstoffen gelangt man, wenn man die Bromierung nach anderen Methoden durchführt, z. B. durch Einwirkung von Brom in Tetrachloräthan oder Nitrobenzol als Suspensionsmittel mit oder ohne Zusatz von Jod als Katalysator.One arrives at similar dyes if one follows the bromination other methods, e.g. B. by the action of bromine in tetrachloroethane or nitrobenzene as a suspending agent with or without the addition of iodine as a catalyst.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48204D DE611338C (en) | 1933-10-26 | 1933-10-26 | Process for the production of halogen-containing Kuepen dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI48204D DE611338C (en) | 1933-10-26 | 1933-10-26 | Process for the production of halogen-containing Kuepen dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE611338C true DE611338C (en) | 1935-03-26 |
Family
ID=7192194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI48204D Expired DE611338C (en) | 1933-10-26 | 1933-10-26 | Process for the production of halogen-containing Kuepen dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE611338C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1095968B (en) * | 1957-05-13 | 1960-12-29 | Bayer Ag | Process for the production of Kuepen dyes |
-
1933
- 1933-10-26 DE DEI48204D patent/DE611338C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1095968B (en) * | 1957-05-13 | 1960-12-29 | Bayer Ag | Process for the production of Kuepen dyes |
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