CH183597A - Process for the production of a new, acidic dye of the anthraquinone series. - Google Patents
Process for the production of a new, acidic dye of the anthraquinone series.Info
- Publication number
- CH183597A CH183597A CH183597DA CH183597A CH 183597 A CH183597 A CH 183597A CH 183597D A CH183597D A CH 183597DA CH 183597 A CH183597 A CH 183597A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- production
- dye
- parts
- anthraquinone series
- Prior art date
Links
- 230000002378 acidificating effect Effects 0.000 title claims description 7
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- OPBOOIFXQHPAPJ-UHFFFAOYSA-N 1-amino-4-anilino-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 OPBOOIFXQHPAPJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- -1 1-amino-1-anilino-anthraquinone-2-sulfonic acid Chemical compound 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen, sauren Farbstoffes der Anthraehinonreihe. Wir haben gefunden, dass ein wertvoller, neuer, saurer Farbstoff der Anthrachinon- reihe erhalten wird, indem man 1-Amino-1- anilino-anthrachinon-2-sulfosäure mit.
einer Alkalimetallverbindung von n-Octylalkohol behandelt, so dass die 2-,Sulfogruppe durch eine n-Oetyloxygruppe ersetzt wird und als dann das Produkt sulfoniert, bis eine Sulfo- säuregruppe eingeführt worden ist. Der Farb stoff ist ein violettes Pulver, welches aus einem schwach sauren Bad auf Wolle violette Töne von hervorragender Wasch-, Walk- und Lichtfestigkeit ergibt.
<I>Beispiel:</I> <B>100</B> Teile Natrium -1- amino - 4 - anilino- anthrachinon-2-sulfona.t, 300 Teile n-Oetyl- alkohol und 50 Teile Ätznatron werden um gerührt und eine Stunde auf 90 C erhitzt. Das Reaktionsgemisch wird dann heiss in ein Gemisch von 2000 Teilen Spiritus und 500 Teilen Wasser eingerührt. Nach Abkühlung auf 35'C wird das- abgeschiedene Produkt abgefiltert, mit kaltem Spiritus gewaschen und durch Rekristallisation aus Aceton ge reinigt.
Das neue Zwischenprodukt: 1-Amino-4- anilino-2-n-Octyloxy-anthrachinon, das sich nach dem Abkühlen aus der Acetonlösung abseheidet; ist eine violette, kristallinische Substanz, welche in konzentrierter Schwefel säure eine bläulich-rote Lösung ergibt und bei 98'C schmilzt.
100 Teile dieses neuen Zwischenproduk tes werden bei 15 bis 20' C in 1000 Teilen 100%iger Schwefelsäure aufgelöst. 250 Teile Oleum (von 25 %<B>SO.,)</B> werden während 1/.1 Stunde bei 15 bis 20' C zugesetzt. Das Gemisch wird 1/.1 Stunde auf<B>25'</B> C erhitzt.
Alsdann wird es in 3500 Teile Eis und Wasser geschüttet, und .die Fällung wird ab g o efiltert. Die Paste wird dann in 7000 Teile Wasser eingerührt, genügend Itznatxon zum Neutralisieren bei<B>80'</B> C zugesetzt, und der Farbstoff wird durch Zusatz von 350 Teilen Kochsalz gefällt. Nach Abkühlung wird er abgefiltert, mit Mger Lauge gewaschen und getrocknet.
Der so erhaltene, neue Farb stoff ist ein violettes Pulver, welches Wolle aus einem schwach sauren Bad in violetten Tönen von hervorragender Wasch-, Walk und Lichtfestigkeit färbt.
Process for the production of a new, acidic dye of the anthraehinone series. We have found that a valuable, new, acidic dye of the anthraquinone series is obtained by adding 1-amino-1-anilino-anthraquinone-2-sulfonic acid with.
treated with an alkali metal compound of n-octyl alcohol so that the 2-sulfo group is replaced by an n-oetyloxy group and then sulfonated the product until a sulfo acid group has been introduced. The dye is a violet powder, which, from a weakly acidic bath on wool, produces violet tones with excellent wash, mill and lightfastness.
<I> Example: </I> <B> 100 </B> parts of sodium -1- amino - 4 - anilino-anthraquinone-2-sulfona.t, 300 parts of n-ethyl alcohol and 50 parts of caustic soda are stirred and heated to 90 C for one hour. The hot reaction mixture is then stirred into a mixture of 2000 parts of spirit and 500 parts of water. After cooling to 35 ° C., the deposited product is filtered off, washed with cold spirit and purified by recrystallization from acetone.
The new intermediate: 1-amino-4-anilino-2-n-octyloxy-anthraquinone, which separates out of the acetone solution after cooling; is a violet, crystalline substance, which in concentrated sulfuric acid gives a bluish-red solution and melts at 98'C.
100 parts of this new intermediate product are dissolved in 1000 parts of 100% sulfuric acid at 15 to 20 ° C. 250 parts of oleum (from 25% SO.) Are added over a period of 1/1 hour at 15 to 20 ° C. The mixture is heated to <B> 25 '</B> C for 1/1 hour.
It is then poured into 3500 parts of ice and water, and the precipitate is filtered off. The paste is then stirred into 7000 parts of water, enough itznatxon is added to neutralize it at 80 ° C, and the dye is precipitated by adding 350 parts of common salt. After cooling, it is filtered off, washed with Mger lye and dried.
The new dye obtained in this way is a violet powder which dyes wool from a weakly acidic bath in violet tones that are extremely washable, fulled and lightfast.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB183597X | 1933-11-28 | ||
| GB140334X | 1934-03-14 | ||
| CH180059T | 1934-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH183597A true CH183597A (en) | 1936-04-15 |
Family
ID=27177667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH183597D CH183597A (en) | 1933-11-28 | 1934-11-17 | Process for the production of a new, acidic dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH183597A (en) |
-
1934
- 1934-11-17 CH CH183597D patent/CH183597A/en unknown
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