CH300792A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH300792A CH300792A CH300792DA CH300792A CH 300792 A CH300792 A CH 300792A CH 300792D A CH300792D A CH 300792DA CH 300792 A CH300792 A CH 300792A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- parts
- sulfonic acid
- preparation
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 aminomonoazo Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000002255 vaccination 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpat"ent Nr. <B>298509.</B> Verfahren zur Herstellung eines Disazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Disazofarbstoff gelangt,
wenn man eine Diazoverbindung des Aminomonoazofarb- stoffes der Formel
EMI0001.0009
worin siell die Sulfonsäuregruppe in<B>-</B> der gleichen Stellung befindet wie die Sulion- säuregruppe der durch Sulion#ierung von 2- N.itro-l-oxybenzol 22<B>-</B> earbonsäLirephenylamid mit schwefeltrioxydhaltiger'Schwefelsäure er hältlichen Sulionsäure, mit 8-Oxychinolin kuppelt.
Der neue Farbstoff bildet ein dunkles ,Pulver, das sich in verdünnten Alkalien mit roter und, in konzentrierter Schwefelsäure mit violetter Farbe löst und Baumwolle nach dem ein- oder zweiba;digen NachImpferungsverfah- ren in wasch- und lichteehten roten Tönen färbt.
Den Aminomonoazolarbstoff der obigen Formel erhält man durch Kupplung von di- azotierter 2-Amino-lroxgbenzol-4-eaeons-äure- phenylamidsulionsäure mit 2-(4-Aminoben- zoyl) <B>-</B> amin#a-5-oxynaph.thalin <B>- 7 -</B> #mIlonsäure. Die Kupplung der Diazoverbindimgen dieses Aminoazofarbstoffes mit dem S-Oxychinolin erfolgt vorteilhaft in alkalischem Medium.
<I>Beispiel:</I> In<B>100,</B> Teile rauchende Schwefelsäure mit 24<B>0/9</B> freiem SO3 trägt man portionen- weise unter gutem Rühren<B>51,6</B> Teile 2-Nitro- 1 <B>-</B> oxybenzol <B>-</B> 4<B>-</B> earbonsäurephenylamid ein. Durch, Aussenkühlung sorgt man dafür, dass die Temperatur nicht Über<B>250</B> steigt. Nach beendigtem Eintragen rührt man, noch<B>30</B> Mi nuten weiter und giesst dann auf Eis.
Hier auf gibt man so viel Natriumhydroxydlösuno, zu, dass das Regktion#sgemiseh nur noch schwach sauer reagiert und. filtriert das im Phenylamidrest sul-fonierte Produkt, ab. Bei der Reduktion nach Bgellamp-Brimmeyr mit Eisen und wenig Essigsäure wird daraus ein helles Produkt erhalten, das sich aus 70pro- zentigem Alkohol umkristallisieren lässt.
3-0,8, Teile des sullonierten und reduzier ten Produktes werden indirekt diazotiert, in- ,dem man diese Menge zusammen mit<B>5,6</B> Tei len Natriumearbonat in<B>1500</B> Teilen Wasser löst, mit -6#9'Teilen Natriumnitrit versetzt und bei<B>0</B> 'bis<B>50</B> zu 40; Teilen 210prozentigür Salz säure und 200, Teilen Wasser fliessen lässt. Nach etwa<B>3</B> Stunden ist die Diazotierung beendet.
Die Diazosuspension wird zur Kupp lung mit<B>135,8</B> Teilen 2-(4!-Am-in(Ybenzoyl)- amino <B>- 5 -</B> oxynaphthalin-7-sulfonsäure in na- triumcailbonatalkalischem Meditim vereinigt.
Der mit Natriumchlorid abgeschiedene, filtrierte und abgepresste Aminomonoazolarlb- stoff -wird in 400 Teilen Wasser unter Zusatz von<B>7</B> Teilen Natriumnitrit angerührt und die entstehende Suspension auf 511 abgekühlt. Hierauf versetzt man mit<B>30</B> 'Teilen 30pro zentiger Salzsäure und rührt etwa 2 Stunden. Die erhaltene Diazoverbindung versetzt man nun mit einer Lösung aus 14,5 Teilen S-Oxy- chinolin. und 12 Teilen 30prozentiger Salz säure in,50 Teilen Wasser.
Anschliessend gibt man<B>50</B> Teile 30prozentige Natriumhydroxyd- lösung dazu und rührt einige Stunden, er wärmt dann auf<B>6:5",</B> fügt<B>100</B> Teile Natrium- chlorid zu, um eine gut filtrie--#bare Form zu erhalten, filtriert und trocknet den Nieder schlag.
Additional patent to main patent no. <B> 298509. </B> Process for the preparation of a disazo dye. It has been found that a valuable disazo dye is obtained
if you use a diazo compound of the aminomonoazo dye of the formula
EMI0001.0009
in which the sulfonic acid group is in the same position as the sulionic acid group of the sulfonic acid group produced by sulionation of 2-Nitro-1-oxybenzene 22 <B> - </B> earbonsäLirephenylamid with sulfur trioxide-containing ' Sulfuric acid is available sulionic acid, coupled with 8-oxyquinoline.
The new dye forms a dark powder which dissolves in dilute alkalis with red and, in concentrated sulfuric acid with violet color, and dyes cotton in washable and light red tones using the one- or two-tone post-vaccination process.
The aminomonoazolar material of the above formula is obtained by coupling diazoated 2-amino-oxybenzene-4-eaeonic acid phenylamidsulionic acid with 2- (4-aminobenzoyl) amine # a-5- oxynaph.thalin <B> - 7 - </B> #milonic acid. The coupling of the diazo compounds of this aminoazo dye with the S-oxyquinoline is advantageously carried out in an alkaline medium.
<I> Example: </I> <B> 100 </B> parts of fuming sulfuric acid with 24 <B> 0/9 </B> free SO3 are added in portions <B> 51.6 with thorough stirring </B> Part 2-nitro- 1 <B> - </B> oxybenzene <B> - </B> 4 <B> - </B> carboxylic acid phenylamide. External cooling ensures that the temperature does not rise above <B> 250 </B>. After the addition is complete, stirring is continued for <B> 30 </B> minutes and then poured onto ice.
Here on you give so much sodium hydroxide solution that the Regktion # sgemiseh only reacts slightly acidic and. the product sulphonated in the phenylamide residue is filtered off. In the Bgellamp-Brimmeyr reduction with iron and a little acetic acid, a light-colored product is obtained that can be recrystallized from 70 percent alcohol.
3-0.8 parts of the sulphonated and reduced product are diazotized indirectly by adding this amount together with <B> 5.6 </B> parts of sodium carbonate in <B> 1500 </B> parts of water dissolves, mixed with -6 # 9 'parts sodium nitrite and at <B> 0 </B>' to <B> 50 </B> to 40; Parts 210 percent hydrochloric acid and 200 parts water. The diazotization is complete after about 3 hours.
The diazo suspension is used for coupling with <B> 135.8 </B> parts of 2- (4! -Am-yn (ybenzoyl) - amino <B> - 5 - </B> oxynaphthalene-7-sulfonic acid in na- triumcailbonate alkaline meditation united.
The aminomonoazolar oxygen separated off with sodium chloride, filtered and pressed out is stirred in 400 parts of water with the addition of 7 parts of sodium nitrite and the resulting suspension is cooled to 511. <B> 30 </B> parts of 30 percent hydrochloric acid are then added and the mixture is stirred for about 2 hours. The diazo compound obtained is then mixed with a solution of 14.5 parts of S-oxyquinoline. and 12 parts of 30 percent hydrochloric acid in 50 parts of water.
Then <B> 50 </B> parts of 30 percent sodium hydroxide solution are added and the mixture is stirred for a few hours, it then warms up to <B> 6: 5 ", </B> adds <B> 100 </B> parts of sodium chloride to obtain an easily filterable form, filters and dries the precipitate.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH300792T | 1951-03-08 | ||
| CH298509T | 1952-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH300792A true CH300792A (en) | 1954-08-15 |
Family
ID=25733962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH300792D CH300792A (en) | 1951-03-08 | 1951-03-08 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH300792A (en) |
-
1951
- 1951-03-08 CH CH300792D patent/CH300792A/en unknown
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