CH148763A - Process for the preparation of poly-azo dyes. - Google Patents
Process for the preparation of poly-azo dyes.Info
- Publication number
- CH148763A CH148763A CH148763DA CH148763A CH 148763 A CH148763 A CH 148763A CH 148763D A CH148763D A CH 148763DA CH 148763 A CH148763 A CH 148763A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- poly
- preparation
- azo dyes
- coupling
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- -1 aminoazo compounds Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WMPTYRGXBUYONY-UHFFFAOYSA-N 2-chloroquinazoline Chemical class C1=CC=CC2=NC(Cl)=NC=C21 WMPTYRGXBUYONY-UHFFFAOYSA-N 0.000 description 1
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung von Poly-Azofarbstofen. Dis- und Tris-Azofarbs.toffe vom Typ Peri-aminona.phtol-sulfosäure + Mittelkom ponente (+ Mittelkomponente) -i- 2-Amino- 5-oxynaphtaIin-7-sulfosäure oder Derivate davon sind durch die deutsche Patentschrift Nr. 1981(12, sowie ihren Zusatz D. R.. P. Nr.<B>202117</B> bekannt geworden.
Die Kupp lung zum Dis- bezw. Trisazofa.rbstoff erfolgt bei diesem Verfahren in soda.alkalischer Lö sung durchwegs mit guter Ausbeute.
Versucht man in analoger Weise Dis- und Poly-Azofarbstoffe aus diazotierten Amino- mono- oder disazoverbindungen, die 1.-Amino- 8-oxynaphtalin oder eines seiner Derivate als Anfangskomponenten enthalten, aufzubauen,
in welchen sich als Endkomponenten an Stelle der 2-Amino-5-oxynaphtalin-7-sulfo- säure oder eines ihrer Derivate ein N-heiero- zyklisch substituiertes 1-Amino-8-oxynaph- talin oder ein Derivat davon befindet, so zeigt es sich, dass in sodaalkalischer oder ammoniakalischer Lösung unvollständige Kupplung eintritt. Die Disazov erbindungeu werden vielmehr grösstenteils zersetzt.
Demgegenüber wurde nun ein Zerfahren gefunden, nach welchem man die Farbstoffe des genannten Type- in guter Ausbeute und vorzüglicher Reinheit herstellen kann. E ist dadurch gekennzeichnet. dass man bei Kupplungen diazotierter Amino-azoverbin- dungen aus diazotierten 1- Amino-8-oxy-naph- talinsulfosäuren und beliebigen Mittelkom- ponenten der aromatischen Reihe mit.
einer N-heterozyklisch substituierten 1- Aniino-8- oxynaphtalin-sulfosäure die letzte Kuplilun in Gegenwart einer Pyridinbase vornimmt.
Man gelangt so zu einem bisher nielit oder sehr schwer zugänglichen wertvollen Farbstofftyp. Die Produkte ziehen überra schend gut auf die pflanzliche Faser in blauen. blaugrünen oder grünen Tönen voi ausgezeichneten Echtheiteii. Befindet .leb ferner in dem heterozyklischen Rest des als Endkomponente verwendeten 1- Amino-8-oxy- naphtalins eine diazotierbare Aminogruppe,
so kann diese Aminogruppe weiterhin ver ändert werden, beispielsweise durch Behand lung mit Säurechloriden oder Anhydriden, (wie Phosgen, Thiophosgen, Essigsäureanhy- drid, Benzoyl- oder Nitrobenzoylchlorid usw.) oder durch Behandlung mit hetero- zyklischen Verbindungen mit beweglichen Halogenatomen, wie Chlorchinazolinen, Chlor- naphtalazinen,
2-Ha,logenbenzothiazolen, Cya- nurchlorid usw. oder auch Weiterdiazotie- rung und -Kupplung in Substanz oder auf der Faser.
<I>Beispiel:</I> Die Diazoverbindung aus 4892 Gewichts teilen des Azofa-rbstoffes aus. dianotierter 1- Amino-8-oxynaphtalin-3.6-disulfosä,ure und 3-Amino-4-kresolmeihy läther wird mit Eis verpastet. Den dünnen Brei gibt man unter Rühren bei 0 bis 5 zu einer Lösung von <B>580</B> Gewichtsteilen des Kondensationsproduk tes aus 1 Teil Cyanurchlorid, 1 Teil 1-Amino- 8-oxynaphtalin-3. 6-disulfosäiir(, lind 1 Teil Anilin.
Das 3-Chloratom ist durch _Ivdroxy1 ersetzt. Die Kupplung erfolgt sofort zu einem blauen Farbstoff, der in der üblichen Weisse aufgearbeitet wird. Er färbt Baum wolle in blauen Tönen von sehr guter Licht echtheit.
Process for the preparation of poly azo dyes. Dis- and Tris-Azofarbs.toffe of the type Peri-aminona.phtol-sulfonic acid + Mittelkom component (+ middle component) -i- 2-amino-5-oxynaphthalen-7-sulfonic acid or derivatives thereof are by the German patent No. 1981 ( 12, as well as its addition DR. P. No. <B> 202117 </B> became known.
The coupling for dis- or. In this process, trisazofa is consistently produced in a soda-alkaline solution with good yield.
If one tries in an analogous way to build up dis- and poly-azo dyes from diazotized amino mono- or disazo compounds which contain 1.-amino-8-oxynaphthalene or one of its derivatives as initial components,
It shows which end components, instead of 2-amino-5-oxynaphthalene-7-sulfonic acid or one of its derivatives, contain an N-heterocyclically substituted 1-amino-8-oxynaphthalene or a derivative thereof that incomplete coupling occurs in soda-alkaline or ammoniacal solution. Rather, the Disazov connections are largely decomposed.
In contrast, a process has now been found by which the dyes of the type mentioned can be produced in good yield and excellent purity. E is indicated by it. that when coupling diazotized amino-azo compounds from diazotized 1-amino-8-oxy-naphthalenesulfonic acids and any middle components of the aromatic series with.
an N-heterocyclically substituted 1-amino-8-oxynaphthalene sulfonic acid makes the last cup in the presence of a pyridine base.
This leads to a valuable type of dye that was previously inaccessible or very difficult to access. The products draw surprisingly well on the plant-based fibers in blue. blue-green or green tones with excellent authenticity. If there is also a diazotizable amino group in the heterocyclic residue of the 1-amino-8-oxynaphthalene used as the end component,
this amino group can be further changed, for example by treatment with acid chlorides or anhydrides (such as phosgene, thiophosgene, acetic anhydride, benzoyl or nitrobenzoyl chloride, etc.) or by treatment with heterocyclic compounds with mobile halogen atoms, such as chloroquinazolines, Chloronaphtalazines,
2-Ha, logenbenzothiazoles, cyanuric chloride etc. or also further diazotization and coupling in substance or on the fiber.
<I> Example: </I> The diazo compound from 4892 parts by weight of the azo dye. Dianotated 1-amino-8-oxynaphthalene-3,6-disulfosä, ure and 3-amino-4-cresolmeihy ether is pasted with ice. The thin paste is added with stirring at 0 to 5 to a solution of <B> 580 </B> parts by weight of the condensation product of 1 part cyanuric chloride and 1 part 1-amino-8-oxynaphthalene-3. 6-disulfosair (, and 1 part aniline.
The 3-chlorine atom has been replaced by _Ivdroxy1. The coupling takes place immediately to give a blue dye, which is worked up in the usual white. It dyes cotton in blue tones that are very lightfast.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE148763X | 1928-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH148763A true CH148763A (en) | 1931-08-15 |
Family
ID=5672914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH148763D CH148763A (en) | 1928-06-18 | 1929-06-08 | Process for the preparation of poly-azo dyes. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH148763A (en) |
-
1929
- 1929-06-08 CH CH148763D patent/CH148763A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE943662C (en) | Process for the preparation of tris and polyazo dyes | |
| DE1077812B (en) | Process for the production of metallizable polyazo dyes | |
| DE574463C (en) | Process for the preparation of water-insoluble monoazo dyes | |
| CH145703A (en) | Process for the preparation of poly-azo dyes. | |
| DE745759C (en) | Process for the production of azo dyes | |
| DE501107C (en) | Process for the preparation of monoazo dyes | |
| DE539725C (en) | Process for making acidic wool azo dyes | |
| DE658017C (en) | Process for the preparation of copper-containing tetrakisazo dyes | |
| DE477912C (en) | Process for the preparation of azo dyes | |
| DE1419840C (en) | Process for the production of reactive dyes | |
| DE551882C (en) | Process for the preparation of water-insoluble azo dyes | |
| DE517437C (en) | Process for the preparation of monoazo dyes | |
| DE557298C (en) | Process for the preparation of substantive polyazo dyes | |
| DE925369C (en) | Process for the production of new copper-containing disazo dyes | |
| AT110261B (en) | Process for the preparation of tetrakisazo dyes. | |
| DE730190C (en) | Process for the preparation of water-soluble disazo dyes | |
| DE453133C (en) | Process for the preparation of trisazo dyes | |
| DE633834C (en) | Process for the production of azo dyes | |
| DE767501C (en) | Process for the preparation of polyazo dyes | |
| DE738900C (en) | Process for the preparation of copper-containing tetrakisazo dyes | |
| DE656379C (en) | Process for the production of azo dyes | |
| DE691991C (en) | Process for the preparation of water-soluble monoazo dyes | |
| DE899535C (en) | Process for the preparation of water-insoluble monoazo dyes | |
| DE623923C (en) | Process for the preparation of tetrakisazo dyes | |
| DE600544C (en) | Process for the preparation of monoazo dyes |