CH267612A - Process for the preparation of an oxyacylaminoazo dye. - Google Patents
Process for the preparation of an oxyacylaminoazo dye.Info
- Publication number
- CH267612A CH267612A CH267612DA CH267612A CH 267612 A CH267612 A CH 267612A CH 267612D A CH267612D A CH 267612DA CH 267612 A CH267612 A CH 267612A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- preparation
- oxyacetylaminoazo
- new
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- 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 claims description 3
- 239000012345 acetylating agent Substances 0.000 claims description 2
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/128—Aliphatic, cycloaliphatic or araliphatic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr.262278. Verfahren zur Herstellung eines Oxyacylaminoazofarhatoffes. Das vorliegende Patent betrifft. ein Ver fahren zur Herstellung eines neuen Oxyacetyl- aniinoazofarbstoffes und ist dadurch gekenn zeichnet, dass man den Monoazofarbstoff, clen man dureh Vereinigen von dianotierter 2-Amino-5-benzoylaminobenzot -1- sulfonsäure mit 2-Ainino-8-oxynaphtalin-6-sitlfonsäure in saurein Medium erhält,
mit Aeetylierungsmit- teln behandelt und hierauf den bei dieser Be handlung mitentstandenen Anteil an N.0- Acetylprodukt durch Einwirkung von Ver- seifungsmitteln in den Oxyacetylaminoazo- farbstoff überführt.
Im Beispiel bedeuten Teile Gewichtsteile. <I>Beispiel:</I> 47 Teile des Monoazofarbstoffes, den man durch Vereinigen von dianotierter 2-Amino- 5 - benzoylaniinobenzol -1- sulfonsäure mit 2- Amino-8-oxynaplithalin-6-sulfonsäiire in sau- , rem Medium erhält, werden in das Gemisch von 50 Teilen Monohydrat und<B>150</B> Teilen Essigsäureanhydrid bei Zimmertemperatur eingetragen und während mehrerer Stunden gerührt.
Die Kondensation ist beendigt., so bald keine freie Ain.inogruppe mehr naehge- wiesen werden kann. Hierauf verdünnt man mit Aceton, wobei das gelbe Acetylierungs- produkt in gut filtrierbarer Form ausfällt. Man filtriert ab, wäscht mit Aceton nach und erwärmt. den Rückstand zwecks Abspaltung des in die Hydroxylgruppe eingetretenen Ace- t.ylrestes während kurzer Zeit in 5prozentiger Sodalösung auf 10 bis 50".
Hierauf salzt man aus, filtriert und trocknet.
Der entstandene Farbstoff, ein rotbraunes Pulver, färbt Wolle in braunstiehi- roten Tönen und kuppelt glatt mit. Diaaoverbindiin- gen. Er löst. sieh in konzentrierter Schwefel säure mit tiefblauer, der Ausgangsfarbstoff dagegen mit roter Farbe.
<B> Additional patent </B> to main patent number 262278. Process for the preparation of an Oxyacylaminoazofarhatoffes. The present patent relates to. a process for the production of a new oxyacetylaniinoazo dye and is characterized in that the monoazo dye is clen by combining dianotated 2-amino-5-benzoylaminobenzot-1-sulfonic acid with 2-amino-8-oxynaphthalene-6-sitlfonic acid preserved in acidic medium,
treated with acetylating agents and then the proportion of N.0-acetyl product that was also formed during this treatment is converted into the oxyacetylaminoazo dye by the action of saponifying agents.
In the example, parts mean parts by weight. <I> Example: </I> 47 parts of the monoazo dye obtained by combining dianotated 2-amino-5-benzoylaniinobenzene-1-sulfonic acid with 2-amino-8-oxynaplithalin-6-sulfonic acid in an acidic medium , are added to the mixture of 50 parts of monohydrate and <B> 150 </B> parts of acetic anhydride at room temperature and stirred for several hours.
The condensation is ended as soon as no more free amino groups can be identified. It is then diluted with acetone, the yellow acetylation product precipitating in a readily filterable form. It is filtered off, washed with acetone and heated. the residue for the purpose of splitting off the acetyl radical which has entered the hydroxyl group for a short time in 5 percent soda solution to 10 to 50 ".
It is then salted out, filtered and dried.
The resulting dye, a reddish-brown powder, dyes wool in brownish-red tones and joins smoothly. Diaao connections. He loosens. See concentrated sulfuric acid with a deep blue color, while the starting dye is red.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267612T | 1946-12-20 | ||
| CH262278T | 1946-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267612A true CH267612A (en) | 1950-03-31 |
Family
ID=25730549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267612D CH267612A (en) | 1946-12-20 | 1946-12-20 | Process for the preparation of an oxyacylaminoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267612A (en) |
-
1946
- 1946-12-20 CH CH267612D patent/CH267612A/en unknown
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