CH134367A - Process for the preparation of a nitrogenous vat dye. - Google Patents
Process for the preparation of a nitrogenous vat dye.Info
- Publication number
- CH134367A CH134367A CH134367DA CH134367A CH 134367 A CH134367 A CH 134367A CH 134367D A CH134367D A CH 134367DA CH 134367 A CH134367 A CH 134367A
- Authority
- CH
- Switzerland
- Prior art keywords
- violet
- reaction
- allowed
- take place
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000984 vat dye Substances 0.000 title claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 244000172533 Viola sororia Species 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- YWVPLPVOZCOMQA-UHFFFAOYSA-N 2,3,4-tribromo-2H-pyranthren-1-one Chemical compound C1=C2C(C(Br)=C(Br)C(C3=O)Br)=C3C=C(C=C3)C2=C2C3=CC3=C(C=CC=C4)C4=CC4=CC=C1C2=C34 YWVPLPVOZCOMQA-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- RYGMFSIKBFXOCR-NJFSPNSNSA-N copper-66 Chemical group [66Cu] RYGMFSIKBFXOCR-NJFSPNSNSA-N 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/70—Benzo-, naphtho-, and anthra-dianthrones
- C09B3/74—Preparation from starting materials already containing the benzo, naphtho-, or anthradianthrone nucleus
- C09B3/76—Preparation from starting materials already containing the benzo, naphtho-, or anthradianthrone nucleus by halogenation
-
- 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
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/70—Benzo-, naphtho-, and anthra-dianthrones
- C09B3/74—Preparation from starting materials already containing the benzo, naphtho-, or anthradianthrone nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung eines stickstoffhaltigen Küpenfarbstoffes. Es wurde gefunden, dass man einen sehr wertvollen neuen Küpenfarbstoff erhält; wenn man Trihalogenpyranthron hergestellt durch Halogenieren von Pyranthron in Chlorsulfon- säure mit 1-Aminoanthrachinon in der Weise umsetzt, dass 1 Mol. Trihalogenpyranthron mit 3 Mol. Aminoanthrachinon reagiert.
Der Farbstoff entsteht zum Beispiel in vorzüglicher Ausbeute, wenn man das Trihalogenpyran- thron mit 1-Aminoanthrachinon erhitzt, wo bei es vorteilhaft ist, in Gegenwart hochsie dender Lösungsmittel zu arbeiten. Statt hochsiedender Lösungsmittel kann man auch hochsiedende Verdünnungsmittel anwenden, und es ist oftmals auch von Vorteil, wenn bei der Umsetzung die Reaktion fördernde Stoffe, wie Katalysatoren, säurebindende Mittel etc. zugegen sind.
Der neue Küpenfarbstoff enthält kein Halogen mehr. Er stellt ein violettschwarzes Pulver dar, das sich in konzentrierter Schwe felsäure mit blauvioletter Farbe löst und Baumwolle aus violetter Küpe in violett schwarzen Tönen anfärbt.
Beispiel: Man kocht während 8 Stunden unter Rühren eine Suspension von 64 Teilen Tri- brompyranthron, 30 Teilen Natriumacetat, 10 Teilen Kupferkarbonat und 66 Teilen 1 Aminoanthrachinon in 500 Teilen Nitrobenzol. Nach dem Erkalten saugt man ab und ent fernt aus dem Rückstand die anorganischen Bestandteile mit Wasser.
Process for the preparation of a nitrogenous vat dye. It has been found that a very valuable new vat dye is obtained; when trihalopyranthrone prepared by halogenating pyranthrone in chlorosulfonic acid is reacted with 1-aminoanthraquinone in such a way that 1 mole of trihalopyranthrone reacts with 3 moles of aminoanthraquinone.
The dye is produced in excellent yield, for example, if the trihalopyranothrone is heated with 1-aminoanthraquinone, where it is advantageous to work in the presence of high-boiling solvents. Instead of high-boiling solvents, high-boiling diluents can also be used, and it is often also advantageous if substances which promote the reaction, such as catalysts, acid-binding agents, etc., are present during the reaction.
The new vat dye no longer contains halogen. It is a violet-black powder that dissolves in concentrated sulfuric acid with a blue-violet color and dyes cotton from a violet vat in violet-black tones.
Example: A suspension of 64 parts of tribromopyranthrone, 30 parts of sodium acetate, 10 parts of copper carbonate and 66 parts of 1 aminoanthraquinone in 500 parts of nitrobenzene is boiled for 8 hours while stirring. After cooling, it is filtered off with suction and the inorganic constituents are removed from the residue with water.
Claims (1)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI30370D DE470948C (en) | 1927-02-18 | 1927-02-18 | Process for the preparation of halogenated Kuepen dyes |
| US199420A US1841961A (en) | 1926-06-30 | 1927-06-16 | Manufacture of vat dyestuffs |
| US296085A US1841966A (en) | 1927-06-16 | 1928-07-28 | Production of vat dyestuffs |
| US296089A US1841963A (en) | 1927-06-16 | 1928-07-28 | Production of vat dyestuffs |
| DEI36415D DE510481C (en) | 1927-06-16 | 1928-12-09 | Process for the preparation of halogen-containing cow dyes |
| GB3820628A GB327175A (en) | 1928-12-27 | 1928-12-27 | Improvements in the manufacture and production of halogenated allo-ms-naphthodianthrones and condensation products thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH134367A true CH134367A (en) | 1929-07-31 |
Family
ID=27544850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH134367D CH134367A (en) | 1927-02-18 | 1928-02-16 | Process for the preparation of a nitrogenous vat dye. |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH134367A (en) |
| DE (1) | DE470948C (en) |
-
1927
- 1927-02-18 DE DEI30370D patent/DE470948C/en not_active Expired
-
1928
- 1928-02-16 CH CH134367D patent/CH134367A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE470948C (en) | 1929-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH134367A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH137397A (en) | Process for the preparation of a nitrogenous vat dye. | |
| DE600102C (en) | Process for the representation of dyes | |
| CH137396A (en) | Process for the preparation of a nitrogenous vat dye. | |
| DE533501C (en) | Process for the preparation of Kuepen dyes | |
| DE446932C (en) | Process for the preparation of Kuepen dyes of the anthraquinone series | |
| DE522689C (en) | Process for the production of Kuepen dyes | |
| DE470949C (en) | Process for the preparation of nitrogenous Kuepen dyes | |
| AT96507B (en) | Process for the preparation of vat dyes and raw materials therefor. | |
| DE495116C (en) | Process for the production of black and gray dyes of the benzanthrone series | |
| DE599795C (en) | Process for the production of Kuepen dyes of the dibenzanthrone series | |
| CH130159A (en) | Process for the preparation of a vat dye of the anthraquinone series. | |
| CH209573A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH144305A (en) | Process for the production of a vat dye of the pyrazole anthrone series. | |
| CH137399A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH140612A (en) | Process for the preparation of a new, nitrogenous vat dye. | |
| CH136265A (en) | Process for the preparation of a valuable vat dye. | |
| CH137398A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH133482A (en) | Process for the preparation of a valuable vat dye. | |
| CH206728A (en) | Process for the production of a new vat dye. | |
| CH140610A (en) | Process for the preparation of a new, nitrogenous vat dye. | |
| CH112805A (en) | Process for the preparation of a vat dye. | |
| CH137400A (en) | Process for the preparation of a nitrogenous vat dye. | |
| CH176813A (en) | Process for the preparation of an anthraquinone derivative. | |
| CH148501A (en) | Process for the preparation of monochloro-3.3'-dichloro-indanthrene. |