CH292690A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH292690A CH292690A CH292690DA CH292690A CH 292690 A CH292690 A CH 292690A CH 292690D A CH292690D A CH 292690DA CH 292690 A CH292690 A CH 292690A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- signifies
- signs
- vat
- 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 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 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 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BGQNFUMJSRPCPC-UHFFFAOYSA-N 1-amino-6-fluoroanthracene-9,10-dione Chemical compound O=C1C2=CC(F)=CC=C2C(=O)C2=C1C=CC=C2N BGQNFUMJSRPCPC-UHFFFAOYSA-N 0.000 description 1
- NRWMRRIIBWACCL-UHFFFAOYSA-N 1-chloro-6-fluoroanthracene-9,10-dione Chemical compound FC1=CC=C2C(=O)C3=C(C=CC=C3Cl)C(=O)C2=C1 NRWMRRIIBWACCL-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C09B1/43—Dicarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 289992. verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, da.ss man zu einem wertvollen Küpenfarbstoff gelangt, wenn man zwei Verbindungen der Formeln
EMI0001.0007
worin das eine der Zeichen X1 und X2 eine NH2-Gruppe und das andere dieser Zeichen ein Halogenatom bedeutet, im molekularen Verhältnis 2:1 miteinander kondensiert.
Der neue Farbstoff löst sieh in konzen trierter Schwefelsäure orangefarben und färbt Baumwolle aus rotvioletter Küpe in kräftigen, reinen gelben Tönen.
Beim vorliegenden Verfahren kann man entweder ein 1-Halogen-6-fhioranthrachinon, vorzugsweise 1-Chlor-6-fluoranthrachinon oder 1-Amino-6-fluoranthrachinon als den einen Ausgangsstoff verwenden. Als zweiter Aus gangsstoff kommt Isophthalsäurediamid oder ein Isophthalsäuredihalogenid, insbesondere das Dichlorid in Betracht.
Die gemäss vorliegendem Verfahren aus zuführenden Kondensationen erfolgen zweck mässig in einem hochsiedenden organischen Lösungsmittel wie Nitrobenzol oder o-Dichlor- benzol und bei erhöhter Temperatur. Bei der Kondensation der 1-Halogen-6-fluoranthrachi- none mit dem Isophthalsäurediamid empfiehlt es sich, dem Reaktionsgemisch ein säurebin dendes Mittel, z. B. Natrium- oder Kalium- , carbonat und ausserdem ein Kupfersalz, wie Kupfer(I)acetat oder Kupfer(I)bromid zu zufügen.
<I>Beispiel:</I> 24 Teile 1-Amino-6-fluorantllrachinon und 10 Teile Isophthalsäuredichlorid werden in 500 Teilen trockenem Nitrobenzol verteilt. Nachdem zwei Stunden bei 135 bis 140 ver rührt wurde, wird erkaltengelassen. Der als goldgelbes Kristallpulver ausfallende Farb stoff wird abgesaugt, gut mit kochendem Alkohol gewaschen und getrocknet.
Additional patent to main patent no. 289992. Process for the production of a vat dye. It has been found that a valuable vat dye can be obtained by using two compounds of the formulas
EMI0001.0007
wherein one of the signs X1 and X2 signifies an NH2 group and the other of these signs signifies a halogen atom, condensed with one another in a molecular ratio of 2: 1.
The new dye dissolves orange in concentrated sulfuric acid and dyes cotton from a red-violet vat in strong, pure yellow tones.
In the present process, either a 1-halo-6-fluoroanthraquinone, preferably 1-chloro-6-fluoroanthraquinone, or 1-amino-6-fluoroanthraquinone can be used as the one starting material. The second starting material is isophthalic acid diamide or an isophthalic acid dihalide, in particular dichloride.
The condensations fed in according to the present process are expediently carried out in a high-boiling organic solvent such as nitrobenzene or o-dichlorobenzene and at elevated temperature. In the condensation of the 1-halo-6-fluoroanthraquinone with the isophthalic acid diamide, it is advisable to add an acid-binding agent to the reaction mixture, eg. B. sodium or potassium, carbonate and also a copper salt such as copper (I) acetate or copper (I) bromide to be added.
<I> Example: </I> 24 parts of 1-amino-6-fluorantllrachinone and 10 parts of isophthalic acid dichloride are distributed in 500 parts of dry nitrobenzene. After stirring for two hours at 135 to 140, it is allowed to cool. The color, which precipitates out as a golden yellow crystal powder, is filtered off with suction, washed well with boiling alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292690T | 1950-07-31 | ||
| CH289992T | 1951-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH292690A true CH292690A (en) | 1953-08-15 |
Family
ID=25732920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH292690D CH292690A (en) | 1950-07-31 | 1950-07-31 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH292690A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870172A (en) * | 1955-11-18 | 1959-01-20 | Sandoz Ag | Pigment dyestuffs of the anthraquinone series |
-
1950
- 1950-07-31 CH CH292690D patent/CH292690A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870172A (en) * | 1955-11-18 | 1959-01-20 | Sandoz Ag | Pigment dyestuffs of the anthraquinone series |
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