CH210517A - Process for the production of a vat dye of the anthraquinone series. - Google Patents
Process for the production of a vat dye of the anthraquinone series.Info
- Publication number
- CH210517A CH210517A CH210517DA CH210517A CH 210517 A CH210517 A CH 210517A CH 210517D A CH210517D A CH 210517DA CH 210517 A CH210517 A CH 210517A
- Authority
- CH
- Switzerland
- Prior art keywords
- diazimide
- dye
- weight
- parts
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000984 vat dye Substances 0.000 title claims description 5
- 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 title claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960003116 amyl nitrite Drugs 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
- 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
- C09B5/26—Carbazoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. <B>205167.</B> Verfahren zur Herstellung eines Küpenfarbstoffes der Anthrachinonreihe. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Herstellung eines Küpenfarb- stoffes der Anthrachinonreihe, welches da durch gekennzeichnet ist, dass man 1.3-Di- (a-anthrachinonylamino)-4. 6-dinitrobenzol zu der entsprechenden 4.6-Diaminoverbindung reduziert,
diese zu dem entsprechenden Di- azimid tetrazotiert, das so erhaltene Diazimid zum Diearbazol verkocht und den so erhal tenen Farbstoff bromiert.
<I>Beispiel:</I> 45 Gewichtsteile 1.3-Di-(a-arithrachino- riylamino)-4.6-diriitrobenzol werden in<B>600</B> Ge wichtsteilen Chlorbenzol in Gegenwart von 511/o Nickelkatalisator bei 120-130' <B>0</B> init Wasserstoff reduziert. Nach Erkalten wird das Reaktionsprodukt abgesaugt und das Diamin aus Nitrobenzol umkristallisiert. Der Schmelzpunkt des reinen Amins liegt bei 346-348<B>0 C.</B> Die Lösungsfarbe in konzen trierter Schwefelsäure ist blau.
<B>31,5</B> Gewichtsteile des so erhaltenen <B>1.</B> 3-Di -(a-arithrachinonylamitio)-4. 6-diamino- benzol, <B>500</B> Gewichtsteile'Eisessig und 132 Ge wichtsteile Amylnitrit werden<B>1</B> Stunde unter Rückfluss zum Sieden erhitzt. Nach dem Er kalten wird abgesaugt und das gelbe Di- azimid aus Nitrobenzol umkristallisiert. Es löst sich gelb in Schwefelsäure und zeigt einen Schmelzpunkt von<B>335 0 C.</B>
<B>29</B> Gewichtsteile Diazimid vom Schmelz punkt 335 <B>0</B> C werden mit<B>290</B> Gewichtstei len Diphenylamin vermischt und unter gutem Rühren<B>10</B> Minuten zum Sieden erhitzt. Nach vorübergehender Lösung und Stick stoffentwicklung scheidet. sich der gebildete Farbstoff dick aus. Die Suspension wird noch warm mit Alkohol verdünnt und abgesaugt. Nach dem Auskochen mit Nitrobenzol, in dem der Farbstoff unlöslich ist, stellt er ein rotbraunes, kristallines Pulver dar.
Er löst sich blau in konzentrierter Schwefelsäure und schmilzt bei 4400<B>0.</B> Der Farbstoff hat folgende Konstitution:
EMI0002.0001
Aus oranger Küpe färbt er auf Baum wolle ein Rotbraun von sehr guter Wasch-, Sodakoch- und Chlorechtheit.
<B>10</B> Gewichtsteile des so erhaltenen Farb stoffes werden in 200 Gewichtsteilen Nitro- benzol mit<B>1</B> Gewichtsteil Jod und<B>7,5</B> (-xe- wichtsteilen Brom auf 160-165' C erwärmt. Nach Beendigung der Bromierung wird bei <B>100-110 0 C</B> abgesaugt, mit warmem Nitro- benzol und heissem Alkohol gewaschen.
Man erhält so einen Dibromfarbstoff, der ans oranger Küpe ein Orange von sehr guten Echtheitseigenschaften färbt.
Das als Ausgangsstoff verwendete 1.3- Di-(a-afithi-achiiiot)ylaiiiitio)-4.6-diiiiti-obetizol kann folgendermassen hergestellt werden: <B>90</B> Gewichtsteile 1-Amir)oai)tlii-aeliii)(iii, 49 (-sewichtsteile 1.3-Dieliloi--4.6-dinitt-obeii- zol vom F.
102-10V <B>C, 22,5</B> Gewichtsteile Natriumcarbonat, 1,2 Gewiehtsteile Kupfer acetat, 1,2 Gewichtsteile Kupferpulver und <B>900</B> Gewichtsteile Nitrobenzol werden<B>10</B> bis 12 Stunden zum Sieden erhitzt. Nach dem Erkalten wird abgesaugt, mit lieif, em Alkohol gewaschen, mit Wasser ausgekocht und getrocknet. Die neue Verbindung wird in einer Ausbeute von<B>83</B> Gewichtsteilen er halten und schmilzt bei<B>360' C.</B> Die Lö sungsfarbe in konzentrierter Schwefelsäure ist grün. Das Umsetztingsprodukt ist chlor- frei. Es kristallisiert aus Nitrobenzol in gelbbraunen Nadeln.
Additional patent to main patent no. <B> 205167. </B> Process for the production of a vat dye of the anthraquinone series. The subject of this additional patent is a process for the production of a vat dye of the anthraquinone series, which is characterized in that 1,3-di- (a-anthraquinonylamino) -4. 6-dinitrobenzene reduced to the corresponding 4,6-diamino compound,
this tetrazotized to the corresponding diazimide, the diazimide obtained in this way boiled to diearbazole and the dye obtained in this way is brominated.
<I> Example: </I> 45 parts by weight of 1,3-di- (a-arithrachino-riylamino) -4.6-diriitrobenzene are converted into <B> 600 </B> parts by weight of chlorobenzene in the presence of 511 / o nickel catalyst at 120-130 '<B> 0 </B> reduced with hydrogen. After cooling, the reaction product is filtered off with suction and the diamine is recrystallized from nitrobenzene. The melting point of the pure amine is 346-348 <B> 0 C. </B> The solution color in concentrated sulfuric acid is blue.
<B> 31.5 </B> parts by weight of the <B> 1. </B> 3-Di - (a-arithraquinonylamitio) -4 thus obtained. 6-diamino-benzene, <B> 500 </B> parts by weight of glacial acetic acid and 132 parts by weight of amyl nitrite are refluxed for <B> 1 </B> hour. After the cold, it is filtered off with suction and the yellow diazimide is recrystallized from nitrobenzene. It dissolves in yellow in sulfuric acid and has a melting point of <B> 335 ° C. </B>
<B> 29 </B> parts by weight of diazimide with a melting point of 335 <B> 0 </B> C are mixed with <B> 290 </B> parts by weight of diphenylamine for <B> 10 </B> minutes with thorough stirring heated to boiling. After a temporary solution and the development of nitrogen, it separates. the dye formed thickly. The suspension is diluted with alcohol while it is still warm and filtered off with suction. After boiling with nitrobenzene, in which the dye is insoluble, it turns into a red-brown, crystalline powder.
It dissolves blue in concentrated sulfuric acid and melts at 4400 <B> 0. </B> The dye has the following constitution:
EMI0002.0001
From an orange vat he dyes a reddish brown on cotton that is very fast to washing, soda boiling and chlorine.
<B> 10 </B> parts by weight of the dye thus obtained are added to 200 parts by weight of nitrobenzene with <B> 1 </B> part by weight of iodine and <B> 7.5 </B> (-xe parts by weight of bromine 160-165 ° C. After the end of the bromination, the mixture is filtered off with suction at 100-110 ° C. and washed with warm nitrobenzene and hot alcohol.
A dibromine dye is obtained in this way, which on the orange vat dyes an orange with very good fastness properties.
The 1.3-di- (a-afithi-achiiiot) ylaiiiitio) -4.6-diiiiti-obetizol used as starting material can be prepared as follows: 90 parts by weight of 1-amir) oai) tlii-aeliii) (iii, 49 (-weight parts 1.3-Dieliloi - 4.6-dinitt-obeiizol vom F.
102-10V <B> C, 22.5 </B> parts by weight of sodium carbonate, 1.2 parts by weight of copper acetate, 1.2 parts by weight of copper powder and 900 parts by weight of nitrobenzene become 10 heated to the boil for up to 12 hours. After cooling, it is filtered off with suction, washed with white alcohol, boiled with water and dried. The new compound is obtained in a yield of <B> 83 </B> parts by weight and melts at <B> 360 ° C. </B> The solution color in concentrated sulfuric acid is green. The reaction product is chlorine-free. It crystallizes from nitrobenzene in yellow-brown needles.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE210517X | 1937-04-09 | ||
| CH205167T | 1938-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210517A true CH210517A (en) | 1940-07-15 |
Family
ID=25724151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210517D CH210517A (en) | 1937-04-09 | 1938-03-31 | Process for the production of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210517A (en) |
-
1938
- 1938-03-31 CH CH210517D patent/CH210517A/en unknown
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