CH164842A - Process for the preparation of an anthraquinone vat dye. - Google Patents
Process for the preparation of an anthraquinone vat dye.Info
- Publication number
- CH164842A CH164842A CH164842DA CH164842A CH 164842 A CH164842 A CH 164842A CH 164842D A CH164842D A CH 164842DA CH 164842 A CH164842 A CH 164842A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone
- parts
- benzoylamino
- vat dye
- agent
- Prior art date
Links
- 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 6
- 150000004056 anthraquinones Chemical class 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 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
- 239000013078 crystal Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CEVURKAAFJXMHE-UHFFFAOYSA-N n-(8-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C=12C(=O)C=3C(Cl)=CC=CC=3C(=O)C2=CC=CC=1NC(=O)C1=CC=CC=C1 CEVURKAAFJXMHE-UHFFFAOYSA-N 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-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
- C09B5/28—Anthrimide carbazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Anthraehinonhiipenfarbstoffes. Es wurde gefunden, dass man einen An- thrachinonküpenfarbstoff herstellen kann, wenn man 1-Benzoylamino-8-halogen-anthra- chinon durch Einwirkung halogenierender Mittel in das 1-Benzoylamino-4. 8-dihalogen- anthrachinon überführt,
hierauf 1 Mol dieses Produktes mit 2 Mol 1-Aminoanthrachinon umsetzt und endlich auf das erhaltene Pro dukt Kondensationsmittel einwirken lässt.
Der so erhaltene Anthrachinonküpenfarb- stoff stellt ein dunkles Pulver dar, das Baumwolle aus der Küpe in braunen Tönen von hervorragender Echtheit färbt.
<I>Beispiel:</I> 100 -Teile 1-Benzoylamino-8-chloranthra- chinon werden in 300 Teilen Nitrobenzol suspendiert. Hierauf werden bei 50 bis 60 150 Teile Sulfurylchlorid zutropfen gelas sen. Nach 20- bis 24stündigem Rühren bei 60 bis<B>70'</B> wird der Kristallbrei abgesaugt, mit wenig Nitrobenzol und hierauf mit Al kohol gewaschen. Das erhaltene 1-Benzoylamino-4.8-di- chloranthraehinon löst sich in kochendem Alkohol und Eisessig schwer, ist dagegen in heissem Nitrobenzol sehr leicht löslich und kristallisiert daraus in sehr feinen gelben Nadeln vom F.
P. 213 his 214 . Diese lösen sich in konz. Schwefelsäure mit roter Farbe; beim Erwärmen der schwefelsauren Lösung auf etwa<B>100'</B> tritt unter Gelbfärbung Ab spaltung .des Benzoylrestes ein.
Eine Mischung von 15,9 Teilen 1-Ben- zoylamino-4. 8-dichloranthrachinon, 20 Tei len 1-Aminoanthrachinon, 0,8 Teilen Kup- ferazetat, 12 Teilen wasserfreiem Natrium azetat und 200 Teilen Naphthalin wird einige Stunden rückfliessend gekocht und hierauf mit ungefähr dem gleichen Volumen Chlor benzol langsam verdünnt. Dann wird bei 70 bis<B>80'</B> filtriert, mit Chlorbenzol, Alkohol und Wasser gewaschen. Hierauf werden die violettbraunen Nadeln getrocknet.
10 Teile,des so erhaltenen Kondensations produktes werden unter Rühren in eine un- ter Kühlung hergestellte Schmelze von 30 Teilen Aluminiumchlorid in 30 Teilen trok- kenem Pyridin bei 80 bis<B>90'</B> eingetragen; hierauf wird während 2 Stunden bei 140 bis 150 gehalten und dann die dunkel gefärbte Schmelze in 1500 Teile Wasser, das durch Zusatz von 150 Volumteilen 30%iger Na tronlauge alkalisch gemacht wurde, eingetra gen.
Bei 40' setzt man 25 Teile Natrium- hydrosulfit zu und filtriert nach etwa einer Viertelstunde die entstandene Küpe von ge ringen Mengen Verunreinigungen. Durch Ausblasen mit Luft wird der Farbstoff ab geschieden, filtriert, gewaschen und getrock net. Der Farbstoff kann durch Behandeln mit Natriumhypochloritlösung gereinigt wer den.
Zu demselben Farbstoffe gelangt man, wenn auf 1-Benzoylamino-8-halogenanthra- chinon statt Sulfurylchlorid ein anderes halo- genierendes Mittel, wie zum Beispiel Chlor oder Brom, einwirken gelassen wird, oder wenn als Kondensationsmittel statt Alumi niumchlorid in Verbindung mit aromatischen Basen, Chlorsulfonsäure oder Aluminium chlorid in Verbindung mit Ammoniak bezw. Natriumchlorid verwendet wird.
Process for the preparation of an anthraquinone thiipene dye. It has been found that an anthraquinone vat dye can be produced if 1-benzoylamino-8-halo-anthraquinone is converted into 1-benzoylamino-4 by the action of halogenating agents. 8-dihalo-anthraquinone converted,
then reacts 1 mole of this product with 2 moles of 1-aminoanthraquinone and finally lets the condensation agent act on the product obtained.
The anthraquinone vat dye thus obtained is a dark powder which dyes cotton from the vat in brown shades of excellent fastness.
<I> Example: </I> 100 parts of 1-benzoylamino-8-chloroanthraquinone are suspended in 300 parts of nitrobenzene. 150 parts of sulfuryl chloride are then added dropwise at 50 to 60. After stirring for 20 to 24 hours at 60 to 70 ', the crystal pulp is filtered off with suction, washed with a little nitrobenzene and then with alcohol. The 1-benzoylamino-4,8-dichloranthraehinone obtained is difficult to dissolve in boiling alcohol and glacial acetic acid, but is very easily soluble in hot nitrobenzene and crystallizes from it in very fine yellow needles of F.
P. 213 to 214. These dissolve in conc. Sulfuric acid with red color; When the sulfuric acid solution is heated to about <B> 100 '</B>, the benzoyl radical is split off with a yellow color.
A mixture of 15.9 parts of 1-benzoylamino-4. 8-dichloroanthraquinone, 20 parts of 1-aminoanthraquinone, 0.8 parts of copper acetate, 12 parts of anhydrous sodium acetate and 200 parts of naphthalene are refluxed for a few hours and then slowly diluted with about the same volume of chlorobenzene. Then it is filtered at 70 to 80 ', washed with chlorobenzene, alcohol and water. The purple-brown needles are then dried.
10 parts of the condensation product thus obtained are introduced with stirring into a melt produced with cooling of 30 parts of aluminum chloride in 30 parts of dry pyridine at 80 to 90 '; it is then held at 140 to 150 for 2 hours and then the dark-colored melt in 1500 parts of water which has been made alkaline by adding 150 parts by volume of 30% sodium hydroxide solution, entered.
At 40 ', 25 parts of sodium hydrosulfite are added and, after about a quarter of an hour, the vat formed is filtered to remove small amounts of impurities. The dye is separated off by blowing out with air, filtered, washed and dried. The dye can be purified by treatment with sodium hypochlorite solution.
The same dye is obtained if 1-benzoylamino-8-halogenanthraquinone is allowed to act on 1-benzoylamino-8-halogenanthraquinone instead of sulfuryl chloride, for example chlorine or bromine, or if the condensation agent is aluminum chloride in combination with aromatic bases Chlorosulfonic acid or aluminum chloride in conjunction with ammonia or. Sodium chloride is used.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH164842T | 1932-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH164842A true CH164842A (en) | 1933-10-31 |
Family
ID=4417778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH164842D CH164842A (en) | 1932-09-15 | 1932-09-15 | Process for the preparation of an anthraquinone vat dye. |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH164842A (en) |
| DE (1) | DE628124C (en) |
| GB (1) | GB414529A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE867724C (en) * | 1942-04-18 | 1953-02-19 | Ciba Geigy | Process for the preparation of dyes of the anthraquinone series |
-
1932
- 1932-09-15 CH CH164842D patent/CH164842A/en unknown
- 1932-09-23 DE DEG83648D patent/DE628124C/en not_active Expired
-
1933
- 1933-09-02 GB GB2439133A patent/GB414529A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE628124C (en) | 1936-03-28 |
| GB414529A (en) | 1934-08-09 |
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