CH267868A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH267868A CH267868A CH267868DA CH267868A CH 267868 A CH267868 A CH 267868A CH 267868D A CH267868D A CH 267868DA CH 267868 A CH267868 A CH 267868A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- azo dye
- production
- new azo
- sulfonic acid
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 9
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 claims description 2
- 230000021736 acetylation Effects 0.000 claims description 2
- 238000006640 acetylation reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 1
- ALIGTWPASYWRKA-UHFFFAOYSA-N NC1=C(C=C(C=C1N)C(C)=O)S(=O)(=O)O Chemical compound NC1=C(C=C(C=C1N)C(C)=O)S(=O)(=O)O ALIGTWPASYWRKA-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000725 suspension 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
- 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
- C09B35/467—D being derived from diaminodiaryl linked through CON<, SO2N<, CSN<
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 264602. Verfahren zur Herstellung eines neuen Azofarbstoffes. Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines neuen Azofarb- stoffes und ist dadurch gekennzeichnet, dass man die Zwischenverbindung aus 4,4'-Tetrazo- benzanilid und 1 Mol Salicylsäure mit dem Diacetyldiaminoazofarbstoff, den man durch saure Kupplung von dianotierter 5-Acetyl- amino-2-aminobenzol-l-sulfonsäure mit 2,
8- Aminonaphthol - 6 - sulfonsäure und nachfol gende Acetylierung erhält, vereinigt und das erhaltene Kupplungsprodukt zwecks Versei fung der im Naphthalinkern sitzenden Ace- tylaminogruppe mit verseifenden Mitteln be handelt.
<I>Beispiel:</I> 22,7 Teile 4,4'-Diaminobenzanilid werden in bekannter Weise tetrazotiert und mit 13,8 Teilen Salicylsäure in alkalischer Lösung zur Zwischenverbindung vereinigt. Zu der orange braunen Suspension derselben.
lässt, man in Gegenwart von 20 Teilen cale. Soda die wäs serige Lösung von 52 Teilen des Monoazofarb- stoffes, den man durch Vereinigung von di anotierter 5-Acetylamino-2-aminobenzol-l-sul- fonsäure mit 2,8-Aminonaphthol-6-sulfonsäure in saurem Medium und nachfolgende Acetylie- rung erhält, bei 5 bis 100 zufliessen. Der ent standene Farbstoff geht mit violettbrauner Farbe in Lösung. Nach beendeter Kupplung wird ausgesalzen, filtriert und getrocknet.
Der so erhaltene Trisazofarbstoff, ein dunkles Pul ver, färbt Baumwolle in lichtechten violett braunen Tönen.
Durch Verseifen in 10 O/oiger Sodalösung bei<B>900</B> erhält man den entsprechenden Amino- azofarbstoff, der Baumwolle in gelbstichig braunen, schweiss- und säureechten Nuancen von guter Lichtechtheit färbt.
Additional patent to main patent No. 264602. Process for the production of a new azo dye. The present patent relates to a process for the production of a new azo dye and is characterized in that the intermediate compound of 4,4'-tetrazo benzanilide and 1 mole of salicylic acid with the diacetyldiaminoazo dye, which is obtained by acidic coupling of dianotated 5-acetyl - amino-2-aminobenzene-l-sulfonic acid with 2,
8-aminonaphthol-6-sulfonic acid and subsequent acetylation is obtained, combined and the coupling product obtained is treated with saponifying agents for the purpose of saponifying the acetylamino group located in the naphthalene nucleus.
<I> Example: </I> 22.7 parts of 4,4'-diaminobenzanilide are tetrazotized in a known manner and combined with 13.8 parts of salicylic acid in alkaline solution to form the intermediate compound. To the orange-brown suspension of the same.
lets, in the presence of 20 parts of cale. Soda is the aqueous solution of 52 parts of the monoazo dye, which is obtained by combining di anotized 5-acetylamino-2-aminobenzene-1-sulphonic acid with 2,8-aminonaphthol-6-sulphonic acid in an acidic medium and subsequent acetylic acid tion receives, inflow at 5 to 100. The resulting dye goes into solution with a violet-brown color. After the coupling has ended, it is salted out, filtered and dried.
The trisazo dye thus obtained, a dark powder, dyes cotton in lightfast violet-brown shades.
Saponification in 10% soda solution at <B> 900 </B> gives the corresponding amino azo dye, which dyes cotton in yellowish brown, sweat- and acid-fast shades of good lightfastness.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267869T | 1947-01-17 | ||
| CH264602T | 1947-01-17 | ||
| CH267868T | 1947-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267868A true CH267868A (en) | 1950-04-15 |
Family
ID=27178090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267868D CH267868A (en) | 1947-01-17 | 1947-01-17 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267868A (en) |
-
1947
- 1947-01-17 CH CH267868D patent/CH267868A/en unknown
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