CH267874A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH267874A CH267874A CH267874DA CH267874A CH 267874 A CH267874 A CH 267874A CH 267874D A CH267874D A CH 267874DA CH 267874 A CH267874 A CH 267874A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- acid
- azo dye
- production
- dianotated
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 10
- 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
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 claims description 3
- AJDFDZADCSRJBN-UHFFFAOYSA-N 3-amino-n-ethyl-n-phenylbenzenesulfonamide Chemical compound C=1C=CC(N)=CC=1S(=O)(=O)N(CC)C1=CC=CC=C1 AJDFDZADCSRJBN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- -1 acetylaminoazo Chemical group 0.000 claims description 3
- 230000021736 acetylation Effects 0.000 claims description 3
- 238000006640 acetylation reaction Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 dianotiertes 1-Aminobenzol-3-sulfonsäure- äthylpheny lam.id mit dem Acetylaminoazo- farbstoff, den man durch saure Kupplung von dianotierter Orthanilsäure mit 2,
8-Aminonaph- thol-6-sulfonsäure und nachfolgende Acetylie- rung erhält,, vereinigt und das erhaltene Kupp lungsprodukt zwecks Verseifung der Acetyl- aminogruppe mit verseifenden Mitteln behan delt.
Beispiel: 46,7 Teile des Acetylaminoazofarbstoffes, den man durch saure Kupplung von dianotier ter Orthanilsäure mit 2,8-Aminonaphthol-6- sulfonsäure und nachfolgende Acetylierung erhält, werden in 250 Teilen Wasser gelöst. Diese Lösung wird mit 20 Teilen cale. Soda deutlich alkalisch gestellt und hierauf unter gutem Rühren mit der Diazoverbindung von 26,1 Teilen dianotiertem 1-Aminobenzol-3-sul- fonsäure-äthylphenylamid bei 0 bis 100 verei nigt.
Sobald keine Diazoverbindung mehr nachgewiesen werden kann, ist die Kupplung beendet. Man salzt aus und filtriert den aus geschiedenen Farbstoff ab. Zur Verseifung der Acetylaminogruppe wird der Farbstoff während etwa einer Stunde in 10 o/oiger Soda lösung auf 900 erwärmt. Nach Beendigung der V erseifung wird der gebildete Farbstoff aus gesalzen, filtriert und getrocknet.
Der neue Farbstoff, ein rotbraunes Pulver, färbt Wolle aus saurem Bade in rotstichig braunen Tönen von guter Licht-, Wasch- und Schweissechtheit.
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 dianotated 1-aminobenzene-3-sulfonic acid ethylphenylamide with the acetylaminoazo dye, which is obtained by acidic coupling of dianotated orthanilic acid with 2 ,
8-aminonaphthol-6-sulfonic acid and subsequent acetylation are obtained, combined and the coupling product obtained is treated with saponifying agents for the purpose of saponifying the acetylamino group.
Example: 46.7 parts of the acetylaminoazo dye, which is obtained by acidic coupling of dianotic orthanilic acid with 2,8-aminonaphthol-6-sulfonic acid and subsequent acetylation, are dissolved in 250 parts of water. This solution is mixed with 20 parts of cale. Soda made clearly alkaline and then combined with the diazo compound of 26.1 parts of dianotated 1-aminobenzene-3-sulphonic acid ethylphenylamide at 0 to 100% with thorough stirring.
As soon as no more diazo compounds can be detected, the coupling is ended. It is salted out and the dyestuff which has separated out is filtered off. To saponify the acetylamino group, the dye is heated to 900 in 10% sodium carbonate solution for about an hour. When the saponification is complete, the dye formed is salted out, filtered and dried.
The new dye, a reddish brown powder, dyes wool from an acid bath in reddish brown tones that are fast to light, washing and perspiration.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267874T | 1947-01-17 | ||
| CH264602T | 1947-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267874A true CH267874A (en) | 1950-04-15 |
Family
ID=25730756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267874D CH267874A (en) | 1947-01-17 | 1947-01-17 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267874A (en) |
-
1947
- 1947-01-17 CH CH267874D patent/CH267874A/en unknown
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