CH291731A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH291731A CH291731A CH291731DA CH291731A CH 291731 A CH291731 A CH 291731A CH 291731D A CH291731D A CH 291731DA CH 291731 A CH291731 A CH 291731A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- process according
- production
- agent
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 5
- YFEHGCGWUWOAFA-UHFFFAOYSA-N 1-amino-6,7-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=C(Cl)C=C2C(=O)C2=C1C=CC=C2N YFEHGCGWUWOAFA-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims 3
- 239000004305 biphenyl Substances 0.000 claims 3
- 125000006267 biphenyl group Chemical group 0.000 claims 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 3
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Küpenfarbstoff gelangt, wenn man 1-Amino-6,7-dichloranthrachinon mit einem den Diphenylsulfon-4-carbonsäurerest abgeben den Mittel behandelt.
Der neue Farbstoff löst sich in konzen trierter Schwefelsäure mit orangeroter Farbe und färbt Baumwolle aus violetter Küpe in cehten, grünstichig gelben Tönen.
Das beim vorliegenden Verfahren als Aus gangsstoff dienende 1- Amino - 6,7 - dichlor- anthrachinon kann durch Mononitrierung von 9,3-Dichloranthrachinon und nachfolgende Re duktion des erhaltenen 1-Nitro-6,7-dichlor- anthraehinons hergestellt werden.
Als den Diphenylsulfon-4-carbonsäurerest abgebendes Mittel kann zweckmässig ein reak tionsfähiges, funktionelles Derivat der Diphe- nylsulfon-4-carbonsäure, beispielsweise ein Säurehalogenid und insbesondere das Säure chlorid, verwendet werden.
Die Umsetzung kann mit Vorteil in indifferenten, hochsieden den Lösungsmitteln, wie Mono-, Di- oder Tri- chlorbenzol, Nitrobenzol oder Naphthalin, ge- wünschtenfalls in Anwesenheit säurebinden der und/oder katalytisch wirksamer Mittel, wie tertiärer Basen (Pyridin oder Dimethyl- anilin), bei erhöhter Temperatur, beispiels weise zwischen 100 und dem Siedepunkt des verwendeten Lösungsmittels, durchgeführt werden.
<I>Beispiel:</I> 33 Teile Diphenylsulfon-4-carbonsäure wer den in 450 Teilen trockenem Nitrobenzol suspendiert und nach Zufügen von 18 Teilen Thionylchlorid und 0,5 Teilen Pyridin andert halb Stunden bei 100 bis 110 verrührt. Nun wird mit 29 Teilen 1-Amino-6,7-dichloranthra- chinon versetzt und zwei Stunden bei 125 bis 130 weitergerührt. Der beim Erkalten in grünstichig gelben Kriställchen ausfallende Farbstoff der Formel
EMI0001.0043
wird abgesaugt, gut mit kochendem Alkohol gewaschen und getrocknet.
Process for the production of a vat dye. It has been found that a valuable vat dye is obtained if 1-amino-6,7-dichloroanthraquinone is treated with an agent which releases the diphenylsulfone-4-carboxylic acid residue.
The new dye dissolves in concentrated sulfuric acid with an orange-red color and dyes cotton from a violet vat in cehten, greenish yellow tones.
The 1-amino-6,7-dichloro-anthraquinone used as starting material in the present process can be prepared by mononitration of 9,3-dichloroanthraquinone and subsequent reduction of the 1-nitro-6,7-dichloroanthraehinone obtained.
A reactive, functional derivative of diphenylsulfone-4-carboxylic acid, for example an acid halide and in particular the acid chloride, can expediently be used as the agent releasing the diphenylsulfone-4-carboxylic acid radical.
The reaction can advantageously be carried out in inert, high-boiling solvents such as mono-, di- or trichlorobenzene, nitrobenzene or naphthalene, if desired in the presence of acid-binding and / or catalytically active agents such as tertiary bases (pyridine or dimethylaniline ), at elevated temperature, for example between 100 and the boiling point of the solvent used.
<I> Example: </I> 33 parts of diphenylsulfone-4-carboxylic acid are suspended in 450 parts of dry nitrobenzene and, after adding 18 parts of thionyl chloride and 0.5 part of pyridine, stirred for one and a half hours at 100 to 110. 29 parts of 1-amino-6,7-dichloroanthraquinone are then added and the mixture is stirred at 125 to 130 for a further two hours. The dye of the formula that precipitates out in greenish yellow crystals when it cools
EMI0001.0043
is suctioned off, washed well with boiling alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH286501T | 1949-07-22 | ||
| CH291731T | 1950-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH291731A true CH291731A (en) | 1953-06-30 |
Family
ID=25732613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH291731D CH291731A (en) | 1949-07-22 | 1950-06-23 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH291731A (en) |
-
1950
- 1950-06-23 CH CH291731D patent/CH291731A/en unknown
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