CH300023A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH300023A CH300023A CH300023DA CH300023A CH 300023 A CH300023 A CH 300023A CH 300023D A CH300023D A CH 300023DA CH 300023 A CH300023 A CH 300023A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- parts
- coupling
- trisazo dye
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 241001366278 Leptotes marina Species 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/463—D being derived from diaminodiphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
Description
Verfahren zur Herstellung eines Trisazofarbstoffes. Es wurde (gefunden, dass man zu einem wertvollen Trisazofarbatoff gelangt, wenn man eine Diazoverbindung der Formel
EMI0001.0007
worin Y eine diazotierte Aminogruppe bedeu tet, mit 2 - OYt naphthalin - 3,6 - disulfonsäure kuppelt.
Der neue Farbstoff bildet ein schwarzes Pulver, das sieh in Wasser leicht löst und eliromgegerbtes Leder in rotstichig marine blauen Tönen färbt.
Die Diazoverbindungen der obigen Formel können hergestellt werden, indem man tetrazo- tiertes 4,4'-Diamino-diphenyl in saurem Me dium einseitig mit 1-Amino-8-oxvnaphthalin- 3;6-disulfonsäure kuppelt und die so erhaltene Verbindung hierauf in alkalischem Medium mit. diazotierter 1.-Aminobenzol-4-sttlfonsäure vereinigt.
Die Kupplung der so erhältlichen Diazodisazoverbindungen mit der 2-Oxvnaph- tlialin-3,6-clisulfonsätire erfolgt zweckmässig in alkalischem Medium.
Beispiel: l1an tetrazotiert 19 Teile 4,4'-Diamino- diplien y1 in bekannter Weise. Zu dieser Tetrazolösung tropft man innert einer Stunde eine klare Lösung von 34,1 Teilen 1-Amino-8- oxvnaphtlialin-3,6-disttlfonsäure in 300 Tei- ).en Wasser, die einen PH-Wert von 5,6 zeigt. Die Temperatur beträgt 10 bis 15 .
Durch all mähliches Zutropfen einer verdünnten, wäs serigen Lösung von Natriumcarbonat stumpft man die bei der Kupplung frei werdende Mine- ralsäure ab, das Gemisch soll aber immer deut lich kongosauer reagieren. Nach zwölf Stun den lässt man bei 5 die Diazoniumlösung aus 17,3 Teilen 1-Aminobenzol-4-sulfonsäure zi1- laufen und stürzt unter kräftigem Rühren eine Lösung von 26 Teilen Natriumcarbonat in 120 Teilen Wasser zum Kupplungsgemisch; der pH-Wert soll nicht höher als 8,5 sein.
Nach 30 Minuten wird eine Lösung aus 30,4; Teilen 2-Oxpnaphthalin-3,6-disulfonsäure und 5 Tei len Natriumcarbonat in 150 Teilen Wasser zu gegeben. Nach zweistündigem Rühren wird durch Zugabe von Salzsäure das Reaktions gemisch schwach sauer gestellt, der abgeschie dene Farbstoff abfiltriert und getroeknet.
Process for the preparation of a trisazo dye. It has been found that a valuable trisazo carbate is obtained by using a diazo compound of the formula
EMI0001.0007
where Y is a diazotized amino group, coupled with 2 - OYt naphthalene - 3,6 - disulfonic acid.
The new dye forms a black powder that dissolves easily in water and dyes Elirom-tanned leather in reddish marine blue tones.
The diazo compounds of the above formula can be prepared by coupling tetrazoated 4,4'-diamino-diphenyl in acidic medium on one side with 1-amino-8-oxvnaphthalene-3; 6-disulfonic acid and then coupling the compound so obtained in alkaline Medium with. diazotized 1.-aminobenzene-4-sttlfonsäure combined.
The coupling of the diazodisazo compounds obtainable in this way with the 2-oxynaphthalene-3,6-clisulfonate is expediently carried out in an alkaline medium.
Example: 19 parts of 4,4'-diamino diplomas y1 tetrazotized in a known manner. A clear solution of 34.1 parts of 1-amino-8-oxvnaphtlialin-3,6-distulfonic acid in 300 parts of water, which has a pH of 5.6, is added dropwise to this tetrazo solution over the course of one hour. The temperature is 10 to 15.
Gradual dropwise addition of a dilute, aqueous solution of sodium carbonate blunted the mineral acid released during the coupling, but the mixture should always be clearly acidic to the Congo. After twelve hours, the diazonium solution of 17.3 parts of 1-aminobenzene-4-sulfonic acid is allowed to run at 5 and a solution of 26 parts of sodium carbonate in 120 parts of water is added to the coupling mixture with vigorous stirring; the pH should not be higher than 8.5.
After 30 minutes a solution of 30.4; Parts of 2-oxpnaphthalene-3,6-disulfonic acid and 5 parts of sodium carbonate in 150 parts of water are added. After two hours of stirring, the reaction mixture is made weakly acidic by adding hydrochloric acid, and the dyestuff deposited is filtered off and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH300023T | 1951-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH300023A true CH300023A (en) | 1954-07-15 |
Family
ID=4490521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH300023D CH300023A (en) | 1951-06-25 | 1951-06-25 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH300023A (en) |
-
1951
- 1951-06-25 CH CH300023D patent/CH300023A/en unknown
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