DE232714C - - Google Patents
Info
- Publication number
- DE232714C DE232714C DENDAT232714D DE232714DA DE232714C DE 232714 C DE232714 C DE 232714C DE NDAT232714 D DENDAT232714 D DE NDAT232714D DE 232714D A DE232714D A DE 232714DA DE 232714 C DE232714 C DE 232714C
- Authority
- DE
- Germany
- Prior art keywords
- oxy
- acenaphthenequinone
- dye
- monoxime
- indoxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- CALLKFAYYAULSN-UHFFFAOYSA-N 2-hydroxyiminoacenaphthylen-1-one Chemical compound C1=CC(C(C2=NO)=O)=C3C2=CC=CC3=C1 CALLKFAYYAULSN-UHFFFAOYSA-N 0.000 claims description 5
- YEQRASMGLPZYDE-UHFFFAOYSA-N Indoxyl Chemical group C1=CC=C[C]2C(O)=CN=C21 YEQRASMGLPZYDE-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- CWRYPZZKDGJXCA-UHFFFAOYSA-N Acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000000984 vat dye Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical class ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000000975 dye Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N Benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N Acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N Pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- -1 nitrous acid ester Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000008096 xylene 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
- C09B7/00—Indigoid dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Description
KAISE RL·QUAY RL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-M 232714 -. KLASSE 22 e. GRUPPE -M 232714 -. CLASS 22 e. GROUP
KALLE & CO. AKT.-GES. in BIEBRICH a. Rh. Verfahren zur Darstellung von Küpenfarbstoffen. Patentiert im Deutschen Reiche vom 12. Oktober 1909 ab. KALLE & CO. ACT.-TOTAL in BIEBRICH a. Rh. Process for the preparation of vat dyes. Patented in the German Empire on October 12, 1909.
Durch Einwirkung von Salpetrigsäureester auf Acenaphten entsteht ein stickstoffhaltiges Oxydationsprodukt des Acenaphtens, das wahrscheinlich das Acenaphtenchinonmonoxim darstellt und unmittelbar mit Indoxyl, Oxythionaphten und ähnlichen Körpern zu Farbstoffen kondensiert werden kann.The action of nitrous acid ester on acenaphthene creates a nitrogenous one Oxidation product of acenaphthene, which is probably acenaphthenequinone monoxime represents and directly with indoxyl, oxythionaphten and similar bodies to dyes can be condensed.
Es wurde nun gefunden, daß dieses Acenaphtenchinonmonoxim häufig einen anscheinend isomeren stickstoffhaltigen Begleiter enthält. Dieser unterscheidet sich vom Acenaphtenchinonmonoxim dadurch, daß er beim Behandeln mit verseifenden Agenzien in der Wärme — z.B. yoprozentiger Schwefelsäure — nicht in Acenaphtenchinon und Hydroxylamin zerfällt, sondern Naphtalsäureanhydrid und Ammoniak liefert. Er kann in der Weise isoliert werden, daß man das Acenaphtenchinonmonoxim durch Auskochen mit Bisulfit davon abtrennt; er hinterbleibt dann als ein kristallinisches, fast farbloses Pulver, das sich in verdünnter Natronlauge mit gelber Farbe löst und auch in Alkohol ziemlich leicht .löslich ist.It has now been found that this acenaphthenequinone monoxime often appears to be contains isomeric nitrogenous companion. This differs from acenaphthenequinone monoxime in that when treated with saponifying agents in the heat - e.g. yo percent sulfuric acid - does not break down into acenaphthenequinone and hydroxylamine, but naphthalic anhydride and Ammonia supplies. It can be isolated in such a way that the acenaphthenequinone monoxime separated from it by boiling with bisulfite; he then remains behind as a crystalline, almost colorless powder that turns yellow in dilute sodium hydroxide solution dissolves and is also fairly easily soluble in alcohol.
Es hat sich nun gezeigt, daß dieser Körper sich vorzüglich zur direkten Überführung in Küpenfarbstoffe eignet durch Kondensation mit Indoxyl, 3-Oxy(i)thionaphten und deren Substitutionsprodukten in Gegenwart von Ameisensäure oder Oxalsäure. Es entsteht beispielsweise durch Kondensation mit3-0xy(i)-thionaphten ein Farbstoff, der mit dem nach dem Verfahren der Patentschrift 205377 er~ haltenen identisch ist. Durch Kondensation mit Indoxyl erhält man den in der Patentschrift 206647 beschriebenen Farbstoff.It has now been shown that this body is ideally suited for direct conversion into vat dyes by condensation with indoxyl, 3-oxy (i) thionaphthene and their substitution products in the presence of formic acid or oxalic acid. For example, it is formed by condensation mit3-0xy (i) -thionaphten a dye that it is identical with the ~ preserved by the method of Patent 205,377th The dye described in patent specification 206647 is obtained by condensation with indoxyl.
20 kg des oben beschriebenen Körpers und τ5 kg 3-Oxy(i)thionaphten werden in etwa 200 kg 90prozentiger, Ameisensäure in der Hitze gelöst. Die Lösung wird sodann so lange am Rückflußkühler gekocht, bis sich kein weiterer Farbstoff mehr bildet. Die. Reaktion kann durch Zugabe einer geringen Menge konzentrierter Schwefelsäure beschleunigt werden. Die Reaktionsmasse, die schon viel abgeschiedenen Farbstoff enthält, wird zwecks völliger. Abscheidung abgekühlt. Der Farbstoff wird dann durch Abfiltrieren, Auswaschen mit Wasser und heißer verdünnter Natronlauge sowie weiteres völliges Auswaschen mit Wasser isoliert.20 kg of the body described above and τ 5 kg of 3-oxy (i) thionaphtene are dissolved in about 200 kg of 90 percent formic acid in the heat. The solution is then refluxed until no more dye is formed. The. The reaction can be accelerated by adding a small amount of concentrated sulfuric acid. The reaction mass, which already contains a lot of deposited dye, becomes more complete. Deposition cooled. The dye is then isolated by filtering it off, washing it out with water and hot, dilute sodium hydroxide solution and then washing it out completely with water.
5555
20 kg des oben beschriebenen stickstoffhaltigen Produktes werden mit 15 kg 3-0xy(i)-thionaphten und 200 kg kristallisierter Oxalsäure in einem mit Rückflußkühler versehenen Kessel zusammengeschmolzen und so lange im Sieden erhalten, bis die Farbstoffbildung beendet ist. Die Isolierung des Kondensationsproduktes geschieht durch Eingießen der Reaktionsmasse in Wasser, Filtrieren und Auswaschen, wie im Beispiel 1 beschrieben ist.20 kg of the nitrogen-containing product described above are mixed with 15 kg of 3-oxy (i) -thionaphthene and 200 kg of crystallized oxalic acid melted together in a boiler equipped with a reflux condenser and so long in the Maintain boiling until dye formation has ended. The condensation product is isolated by pouring the reaction mass in water, filtering and washing as described in Example 1.
20 kg des oben bezeichneten. Körpers werden mit 15 kg 3-Oxy(i)thionaphten und 200 kg Pentachloräthan oder einem anderen indifferenten Lösungsmittel, wie z. B. Xylol, unter Zusatz von Ameisensäure oder Oxalsäure in20 kg of the above. Body will be with 15 kg 3-Oxy (i) thionaphten and 200 kg Pentachloroethane or another inert solvent, such as. B. xylene, under Addition of formic acid or oxalic acid in
einem mit Rückflußkühler versehenen Gefäß gekocht. Der Farbstoff wird durch Abkühlen abgeschieden und durch Filtration und Auswaschen isoliert.boiled in a vessel equipped with a reflux condenser. The dye is made by cooling deposited and isolated by filtration and washing.
In den vorstehenden Beispielen kann man das 3 - Oxy(i)thionaphten durch seine Carbonsäure und durch die Substitutionsprodukte dieser Verbindungen ersetzen. In gleicher Weise kann man auch an Stelle des 3-0xy(i)-thionaphtens das Indoxyl und seine Derivate benutzen.In the above examples, 3-oxy (i) thionaphthene can be obtained through its carboxylic acid and replace them with the substitution products of these compounds. In the same One can also instead of 3-oxy (i) -thionaphthene use the indoxyl and its derivatives.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE232714C true DE232714C (en) |
Family
ID=492720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT232714D Active DE232714C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE232714C (en) |
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- DE DENDAT232714D patent/DE232714C/de active Active
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