DE1099543B - Process for the preparation of 1, 4-, 1, 5- and 1,8-diaminoanthraquinones monosubstituted on an amino group - Google Patents
Process for the preparation of 1, 4-, 1, 5- and 1,8-diaminoanthraquinones monosubstituted on an amino groupInfo
- Publication number
- DE1099543B DE1099543B DEB52258A DEB0052258A DE1099543B DE 1099543 B DE1099543 B DE 1099543B DE B52258 A DEB52258 A DE B52258A DE B0052258 A DEB0052258 A DE B0052258A DE 1099543 B DE1099543 B DE 1099543B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- diaminoanthraquinones
- phenyl
- monosubstituted
- amino group
- 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.)
- Pending
Links
- 125000003277 amino group Chemical group 0.000 title claims description 8
- QWXDVWSEUJXVIK-UHFFFAOYSA-N 1,8-diaminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC(N)=C2C(=O)C2=C1C=CC=C2N QWXDVWSEUJXVIK-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- UTSOANOTPZSYJK-UHFFFAOYSA-N 4-chloro-6-phenyl-1,3,5-triazin-2-amine Chemical compound NC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 UTSOANOTPZSYJK-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- OBHKONRNYCDRKM-UHFFFAOYSA-N 4-chloro-2-phenylquinazoline Chemical compound N=1C2=CC=CC=C2C(Cl)=NC=1C1=CC=CC=C1 OBHKONRNYCDRKM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 240000009038 Viola odorata Species 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 2
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- -1 amine hydrochloride Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JZLDXVVDXPWOBH-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione hydrochloride Chemical compound Cl.O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N JZLDXVVDXPWOBH-UHFFFAOYSA-N 0.000 description 1
- PFQKVIPWUJHPIH-UHFFFAOYSA-N 4-chloro-n,6-diphenyl-1,3,5-triazin-2-amine Chemical compound N=1C(C=2C=CC=CC=2)=NC(Cl)=NC=1NC1=CC=CC=C1 PFQKVIPWUJHPIH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- C09B1/36—Dyes with acylated amino groups
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von an einer Aminogruppe monosubstituierten 1,4-, 1,5- und 1,8-Diaminoanthrachinonen Es wurde gefunden, daß man leicht und mit guter Ausbeute an einer Aminogruppe monosubstituierte 1,4-, 1,5- und 1,8-Diaminoanthrachinone und ihre Hydrochloride erhält, wenn man 1,4-, 1,5- oder 1,8-Diaminoanthrachinon in Gegenwart eines gesättigten Lactams, das am Stickstoff durch einen Alkylrest substituiert sein kann, bei erhöhter Temperatur mit 2-Phenyl-4-chlorchinazolin oder mit 2-Phenyl-4-anilino-6-chlor-1,3,5-triazin umsetzt und gegebenenfalls das als Reaktionsprodukt erhaltene Hydrochlorid des an einer Aminogruppe monosubstituierten 1,4-, 1,5- oder 1,8-Diaminoanthrachinons in an sich bekannter Weise in die freie Base überführt.Process for the preparation of monosubstituted on an amino group 1,4-, 1,5- and 1,8-diaminoanthraquinones It has been found that easily and with good yield of 1,4-, 1,5- and 1,8-diaminoanthraquinones monosubstituted at one amino group and their hydrochlorides are obtained by using 1,4-, 1,5- or 1,8-diaminoanthraquinone in the presence of a saturated lactam, which is attached to nitrogen by an alkyl radical can be substituted at elevated temperature with 2-phenyl-4-chloroquinazoline or with 2-phenyl-4-anilino-6-chloro-1,3,5-triazine and optionally the as Hydrochloride obtained from the reaction product of the monosubstituted on an amino group 1,4-, 1,5- or 1,8-diaminoanthraquinones in a manner known per se into the free Base transferred.
Geeignete gesättigte Lactame sind z. B. das Pyrrolidon, Piperidon, Caprolactam, Capryllactam oder ihre N-Alkylderivate.Suitable saturated lactams are e.g. B. the pyrrolidone, piperidone, Caprolactam, capryllactam or their N-alkyl derivatives.
Das neue Verfahren hat den Vorteil, daß sich die Ausgangsstoffe in den Lactamen leicht lösen, während die als Hydrochloride anfallenden Monoumsetzungsprodukte schwer- bis unlöslich sind und daher im allgemeinen in der Kälte ausfallen. Erforderlichenfalls kann man ihre Abscheidung durch Zusatz von Wasser fördern.The new process has the advantage that the starting materials are in the lactams dissolve easily, while the mono-conversion products obtained as hydrochlorides are poorly or insoluble and therefore generally precipitate in the cold. If necessary their separation can be promoted by adding water.
Im Gegensatz zu der aus der deutschen Patentschrift 921533 bekannten Arbeitsweise erhält man nach dem erfindungsgemäßen Verfahren auch bei Verwendung eines Überschusses von 2-Phenyl-4-chlorchinazolin oder 2-Phenyl-4-anilino-6-chlorcyanidin praktisch kein an beiden Aminogruppen umgesetztes Produkt, sondern nur das Monoumsetzungsprodukt mit einer freien Aminogruppe, wobei die Ausbeuten durchweg sehr gut sind.In contrast to the procedure known from German patent specification 921533, practically no product reacted on both amino groups is obtained in the process according to the invention, even when using an excess of 2-phenyl-4-chloroquinazoline or 2-phenyl-4-anilino-6-chlorocyanidine, but only the mono-reaction product with a free amino group, and the yields are consistently very good.
Die erfindungsgemäß leicht zugänglichen Produkte können in wertvolle Küpenfarbstoffe umgewandelt werden.The easily accessible products according to the invention can be used in valuable Vat dyes are converted.
Die in den Beispielen genannten Teile sind Gewichtsteile. Beispiel 1 In ein Gemisch aus 50 Teilen 1,4-Diaminoanthrachinon und 450 Teilen N-Methylpyrrolidon werden bei 950C portionsweise 50 g 2-Phenyl-4-chlorchinazolin eingetragen. Man behält diese Temperatur nach beendetem Eintragen noch 1 Stunde lang bei, läßt dann auf 60°C abkühlen, saugt das Reaktionsprodukt ab, wäscht es mit wenig N-Methylpyrrolidon undmit viel Methanol und trocknet es. Man erhält 84 Teile 1-Amino-4-(2'-phenylchinazolyl-(4'))-aminoanthrachinonhydrochlorid in Form prächtiger blauvioletter Kristalle. Um das freie Amin zu erhalten, löst man das Hydrochlorid in konzentrierter Schwefelsäure, läßt diese Lösung unter Rühren in Eiswasser einfließen, sammelt das ausfallende Produkt auf einer Nutsche und wäscht es säurefrei. Man erhält blaue Kristalle vom Schmelzpunkt 273 bis 278°C.The parts mentioned in the examples are parts by weight. example 1 In a mixture of 50 parts of 1,4-diaminoanthraquinone and 450 parts of N-methylpyrrolidone 50 g of 2-phenyl-4-chloroquinazoline are added in portions at 950C. One keeps this temperature for 1 hour after the end of the entry, then leaves on Cool to 60 ° C, the reaction product is filtered off with suction and washed with a little N-methylpyrrolidone and with a lot of methanol and dry it. 84 parts of 1-amino-4- (2'-phenylquinazolyl- (4 ')) -aminoanthraquinone hydrochloride are obtained in the form of magnificent blue-violet crystals. To get the free amine, dissolve if the hydrochloride is dissolved in concentrated sulfuric acid, this solution is left with stirring Pour into ice water, collects the precipitated product on a suction filter and washes it acid free. Blue crystals with a melting point of 273 to 278 ° C. are obtained.
Verwendet man an Stelle von 50 Teilen 2-Phenyl-4-chlorchinazolin 100 Teile 2-Phenyl-4-chlorchinazolin und arbeitet im übrigen, wie im ersten Absatz angegeben, weiter, so erhält man 84 Teile 1-Amino-4-(2'-phenylchinazolyl-(4'))-aminoanthrachinonhydrochlorid in Form eines blauvioletten Kristallpulvers. Beispiel 2 Zur Herstellung von 1-Amino-5-(2'-phenylchinazolyl-(4'))-aminoanthrachinon arbeitet man, wie im Beispiel 1 beschrieben, geht jedoch vom 1,5-Diaminoanthrachinon aus. Das Hydrochlorid des Amins fällt in Form kupferfarbener Kristalle in einer Ausbeute von 70 Teilen an. Es kann, wie im Beispiel 1 beschrieben, in das freie Amin übergeführt werden, das einen Schmelzpunkt von 303 bis 304°C aufweist.Use 2-phenyl-4-chloroquinazoline 100 instead of 50 parts Parts 2-phenyl-4-chloroquinazoline and otherwise works as indicated in the first paragraph, furthermore, 84 parts of 1-amino-4- (2'-phenylquinazolyl- (4 ')) aminoanthraquinone hydrochloride are obtained in the form of a blue-violet crystal powder. Example 2 For the preparation of 1-amino-5- (2'-phenylquinazolyl- (4 ')) -aminoanthraquinone if you work as described in Example 1, but you start from 1,5-diaminoanthraquinone the end. The amine hydrochloride falls in the form of copper-colored crystals in a Yield of 70 parts. It can, as described in Example 1, in the free Amine are converted, which has a melting point of 303 to 304 ° C.
Beispiel 3 In ein Gemisch aus 24 Teilen 1,5-Diaminoanthrachinon und 240 Teilen N-Methylpyrrolidon, werden bei 120'C innerhalb einer Stunde unter Rühren 28 Teile 2-Phenyl-4-chlor-6-anilino-triazin-(1,3,5) eingetragen. Man hält 2 Stunden lang bei 120°C und läßt dann erkalten. Die klare Lösung rührt man in Wasser ein. Dabei wird das bei der Umsetzung zunächst entstandene Hydrochlorid in die freie Base übergeführt. Man saugt das ausgeschiedene Produkt ab, wäscht es mit Wasser und trocknet es. Man erhält 47 Teile 1-Amino-5-(2'-phenyl-4'-anilinotriazinyl-6')-aminoanthrachinon in Form von roten Kristallen vom Schmelzpunkt 283 bis 285°C.Example 3 In a mixture of 24 parts of 1,5-diaminoanthraquinone and 240 parts of N-methylpyrrolidone, are at 120'C within one hour with stirring 28 parts of 2-phenyl-4-chloro-6-anilino-triazine (1.3 , 5) registered. It is kept at 120 ° C. for 2 hours and then allowed to cool. The clear solution is stirred into water. The hydrochloride initially formed in the reaction is converted into the free base. The precipitated product is filtered off with suction, washed with water and dried. 47 parts of 1-amino-5- (2'-phenyl-4'-anilinotriazinyl-6 ') -aminoanthraquinone are obtained in the form of red crystals with a melting point of 283 to 285.degree.
Das als Ausgangsmaterial verwendete 2-Phenyl-4-chlor-6-anilinotriazin-(1,3,5) kann wie folgt hergestellt werden: In 150 Teilen Wasser löst man 7,0 Teile wasserfreies Kaliumcarbonat, setzt 9,3 Teile Anilin hinzu und läßt schließlich unter gutem Rühren eine Lösung von 22,6 Teilen 2-Phenyl-4,6-dichlortriazin-(1,3,5) in 100 Teilen Aceton zufließen. Das Gemisch wird 1 Stunde -bei 20 bis 30°C gerührt. Dann saugt man den ausgeschiedenen Kristallbrei ab, wäscht ihn mit Wasser aus und trocknet ihn. Die Ausbeute beträgt 27 Teile -2-Phenyl.-4-chlor-6-anüinotriazin-(1,3,5). Die farblosen Kristalle schmelzen bei. 160 bis 164°C.The 2-phenyl-4-chloro-6-anilinotriazine- (1,3,5) used as starting material can be prepared as follows: 7.0 parts of anhydrous water are dissolved in 150 parts of water Potassium carbonate, 9.3 parts of aniline are added and finally left with thorough stirring a solution of 22.6 parts of 2-phenyl-4,6-dichlorotriazine- (1,3,5) in 100 parts of acetone flow in. The mixture is stirred at 20 to 30 ° C. for 1 hour. then The precipitated crystal pulp is sucked off, washed out with water and dried him. The yield is 27 parts of -2-phenyl-4-chloro-6-anuinotriazine- (1,3,5). the colorless crystals melt at. 160 to 164 ° C.
Beispiel 4 24 Teile 1,4-Diaminoanthrachinon werden in. 100 Teilen Caprolactam bei 95 bis 100°C gelöst und in die Lösung bei dieser Temperatur 24,5 Teile 2-Phenyl-4-chlorchinazolin innerhalb von 5 Minuten -eingetragen. Das Umsetzungsgemisch hält- man. noch 1 Stunde lang bei 95 bis 100°C und trägt es sodann noch heiß in 350 Teile Wasser ein. Das sich abscheidende Umsetzungsgut saugt man ab, wäscht es mit Wasser und Methanol und. trocknet es. Man erhält 45 Teile 1-Amin.o-4-(2'-phenylchinazolyl-(4'))-aminoanthrachinonhydrochlorid in Form blauvioletter Nadeln. Das Produkt ist mit dem nach Beispiel 1 erhältlichen Hydrochlorid identisch.Example 4 24 parts of 1,4-diaminoanthraquinone are in 100 parts Caprolactam dissolved at 95 to 100 ° C and in the solution at this temperature 24.5 Parts of 2-phenyl-4-chloroquinazoline entered within 5 minutes. The implementation mix hold- man. 1 hour at 95 to 100 ° C and then wears it in while still hot 350 parts of water. The reaction material that separates out is suctioned off and washed with water and methanol and. it dries. 45 parts of 1-amin.o-4- (2'-phenylquinazolyl- (4 ')) -aminoanthraquinone hydrochloride are obtained in the form of blue-violet needles. The product is obtainable with that according to Example 1 Hydrochloride identical.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB52258A DE1099543B (en) | 1957-05-08 | 1957-05-08 | Process for the preparation of 1, 4-, 1, 5- and 1,8-diaminoanthraquinones monosubstituted on an amino group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB52258A DE1099543B (en) | 1957-05-08 | 1957-05-08 | Process for the preparation of 1, 4-, 1, 5- and 1,8-diaminoanthraquinones monosubstituted on an amino group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1099543B true DE1099543B (en) | 1961-02-16 |
Family
ID=6969837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB52258A Pending DE1099543B (en) | 1957-05-08 | 1957-05-08 | Process for the preparation of 1, 4-, 1, 5- and 1,8-diaminoanthraquinones monosubstituted on an amino group |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1099543B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270713B (en) * | 1960-12-01 | 1968-06-20 | Ciba Geigy | Process for the preparation of anthraquinone dyes |
| WO1991000317A1 (en) * | 1989-06-30 | 1991-01-10 | Basf Aktiengesellschaft | Method of preparing anthraquinone dyes |
-
1957
- 1957-05-08 DE DEB52258A patent/DE1099543B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270713B (en) * | 1960-12-01 | 1968-06-20 | Ciba Geigy | Process for the preparation of anthraquinone dyes |
| WO1991000317A1 (en) * | 1989-06-30 | 1991-01-10 | Basf Aktiengesellschaft | Method of preparing anthraquinone dyes |
| US5210190A (en) * | 1989-06-30 | 1993-05-11 | Basf Aktiengesellschaft | Preparation of triazinyl-bis-anthraquinone dyes by reacting aryldihalotriazine with amino anthraquinone |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1924249C3 (en) | Nitro-p-phenylenediamines, process for the N-monomethylation of nitroanilines and nitro-p-phenylenediamines and use of the N-monomethylnitroanilines for dyeing hair | |
| DE1099543B (en) | Process for the preparation of 1, 4-, 1, 5- and 1,8-diaminoanthraquinones monosubstituted on an amino group | |
| DE1067439B (en) | Process for the preparation of 1,3,4-oxdiazoles | |
| DE935566C (en) | Process for the production of Kuepen dyes | |
| DE695646C (en) | Process for the preparation of nitrogen-containing compounds and dyes of the anthraquinone series | |
| DE287373C (en) | ||
| DE607677C (en) | Process for the production of nitrogen-containing condensation products | |
| DE696370C (en) | Process for the production of Kuepen dyes of the anthraquinone series | |
| DE1127911B (en) | Process for the preparation of 1-amino-2- (ªÏ-mono- and -dichlor- or -bromoacetyl) -anthraquinones | |
| DE1644306C3 (en) | Basic anthraquinone and nitro dyes and processes for their preparation | |
| DE498052C (en) | Process for the preparation of 1-arylaminoanthraquinone-2-carboxylic acid esters | |
| DE911493C (en) | Process for the preparation of 2- (1, 4-diamino-2-anthraquinonyl) -1, 3, 4-oxydiazoles | |
| DE2250107A1 (en) | PROCESS FOR THE PRODUCTION OF 1,1'DIANTHRAQUINONYLENE | |
| DE846592C (en) | Process for the production of Kuepen dyes | |
| DE205881C (en) | ||
| DE748375C (en) | Process for the production of condensation products | |
| DE732041C (en) | Process for the production of chromable dyes of the phthalein series | |
| DE232785C (en) | ||
| DE678556C (en) | Process for the production of anthraquinone dyes | |
| DE2631040A1 (en) | PROCESS FOR THE PRODUCTION OF BASIC OXAZINE DYES | |
| DE2359411C3 (en) | Anthraquinone dyes containing sulfonic acid groups, their preparation and their use | |
| DE430901C (en) | Process for the preparation of Kuepen dyes of the anthraquinone series | |
| DE529649C (en) | Process for the preparation of anthraquinone dyes | |
| AT29055B (en) | Process for the preparation of vat dyes of the anthracene series. | |
| CH358180A (en) | Process for the production of vat dyes |