CH200537A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH200537A CH200537A CH200537DA CH200537A CH 200537 A CH200537 A CH 200537A CH 200537D A CH200537D A CH 200537DA CH 200537 A CH200537 A CH 200537A
- Authority
- CH
- Switzerland
- Prior art keywords
- vat dye
- parts
- production
- condensed
- bromobenzanthrone
- Prior art date
Links
- 239000000984 vat dye Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000007859 condensation product Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- DGJNWQJOASAMHY-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)Cl)=CC=C3C(=O)C2=C1 DGJNWQJOASAMHY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 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
- 238000009835 boiling Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WITKIIIPSSFHST-UHFFFAOYSA-N 1-[(9,10-dioxoanthracen-1-yl)amino]anthracene-9,10-dione Chemical compound 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 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-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
- 240000007817 Olea europaea Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- DAZLBCIMRZNCRV-UHFFFAOYSA-N aniline;sodium Chemical compound [Na].NC1=CC=CC=C1 DAZLBCIMRZNCRV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007858 starting material 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
- 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
- C09B5/2409—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 not provided for in one of the sub groups C09B5/26 - C09B5/62
- C09B5/2436—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 not provided for in one of the sub groups C09B5/26 - C09B5/62 only nitrogen-containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 194458. Verfahren zur Herstellung eines güpenfarbstoifes. Vorliegendes Patent bezieht sich auf ein Verfahren zur Herstellung eines Küpenfarb- stoffes, dadurch gekennzeichnet, dass man 5,5'-Diamino-diphthaloylcarbazol mit Bz1- Brombenzanthron kondensiert und das Kon densationsprodukt der Formel:
EMI0001.0009
ein alkalisches Kondensationsmittel und An- thrachinon-2-carlionsäurechlorid aufeinander einwirken lässt.
Der neue Küpenfarbstoff löst sich in kon zentrierter Schwefelsäure mit blaustichig- grüner Farbe und färbt die pflanzliche Faser aus brauner Küpe in sehr echten Khakitönen. <I>Beispiel 1:</I> 45 Teile 5,5'-Diamino-diphthaloylearbazol werden mit 31 Teilen Bzl-Brombenzanthron kondensiert und dieses Kondensationsprodukt mit alkoholischem Kali verschmolzen. (Das erhaltene Produkt löst sich in konzentrierter Schwefelsäure mit olivgrüner Farbe.
Aus konzentrierter Schwefelsäure umgelöst; färbt es aus brauner Küpe Baumwolle in dunkel braunen Tönen.) 68 Teile dieses Produktes der Formel-
EMI0002.0012
werden in fein verteilter Form in 1000 Teilen o-Dichlorbenzol mit 30 Teilen Anthrachinon- 2-carbonsäurechlorid durch mehrstündiges Kochen kondensiert. Der gebildete Farbstoff wird noch heiss abgesaugt, gewaschen und ge trocknet.
Beispiel <I>2:</I> 45 Teile 5,5'-Diamino-diphthaloylcarbazol werden mit 31 Teilen Bzl-Brombenzanthron kondensiert. Das so erhaltene Kondensations produkt wird in fein verteilter Form in 1000 Teilen o-Dichlorbenzol durch mehrstün diges Kochen mit 30 Teilen Anthrachinon=2- carbonsäurechlorid kondensiert.
91 Teile des so erhaltenen Anthrimids der Formel:
EMI0002.0025
werden bei etwa 140 C in eine Lösung von 250 Teilen Natriumanilin in etwa 800 Tei len wasserfreiem Anilin eingetragen. Unter Durchleiten von Stickstoff hält man die Re aktionsmasse bei dieser Temperatur, bis kein unverändertes Ausgangsmaterial mehr vor handen ist: Die erkaltete Schmelze wird auf überschüssige verdünnte Salzsäure gegossen, der Niederschlag abgesaugt, gewaschen und getrocknet.
Additional patent to main patent No. 194458. Process for the production of a güpenfarbstoifes. The present patent relates to a process for the production of a vat dye, characterized in that 5,5'-diamino-diphthaloylcarbazole is condensed with Bz1-bromobenzanthrone and the condensation product of the formula:
EMI0001.0009
an alkaline condensing agent and anthraquinone-2-carlionic acid chloride can act on one another.
The new vat dye dissolves in concentrated sulfuric acid with a bluish green color and colors the vegetable fibers from the brown vat in very real khaki tones. <I> Example 1: </I> 45 parts of 5,5'-diamino-diphthaloylearbazole are condensed with 31 parts of Bzl-bromobenzanthrone and this condensation product is fused with alcoholic potash. (The product obtained dissolves in concentrated sulfuric acid with an olive green color.
Dissolved from concentrated sulfuric acid; dyes it from brown cotton vat in dark brown shades.) 68 parts of this product of the formula
EMI0002.0012
are condensed in finely divided form in 1000 parts of o-dichlorobenzene with 30 parts of anthraquinone-2-carboxylic acid chloride by boiling for several hours. The dye formed is filtered off with suction while hot, washed and dried.
Example <I> 2: </I> 45 parts of 5,5'-diamino-diphthaloylcarbazole are condensed with 31 parts of Bzl-bromobenzanthrone. The condensation product thus obtained is condensed in finely divided form in 1000 parts of o-dichlorobenzene by boiling for several hours with 30 parts of anthraquinone = 2-carboxylic acid chloride.
91 parts of the anthrimide thus obtained of the formula:
EMI0002.0025
are entered at about 140 C in a solution of 250 parts of sodium aniline in about 800 parts of anhydrous aniline. While passing nitrogen through, the reaction mass is kept at this temperature until there is no longer any unchanged starting material: the cooled melt is poured onto excess dilute hydrochloric acid, and the precipitate is filtered off with suction, washed and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200537X | 1935-08-10 | ||
| CH194458T | 1936-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200537A true CH200537A (en) | 1938-10-15 |
Family
ID=25722686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200537D CH200537A (en) | 1935-08-10 | 1936-08-07 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200537A (en) |
-
1936
- 1936-08-07 CH CH200537D patent/CH200537A/en unknown
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