CH267624A - Process for the preparation of an oxyacylaminoazo dye. - Google Patents
Process for the preparation of an oxyacylaminoazo dye.Info
- Publication number
- CH267624A CH267624A CH267624DA CH267624A CH 267624 A CH267624 A CH 267624A CH 267624D A CH267624D A CH 267624DA CH 267624 A CH267624 A CH 267624A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- preparation
- sulfonic acid
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 12
- YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012345 acetylating agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 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 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
- 239000002253 acid Substances 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient 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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 262278. Verfahren zur Herstellung eines Oxyaeylaminoazofarbatoffes. Das vorliegende Patent betrifft ein Ver fahren zur Herstellung eines neuen Oxyacetyl- aminoazofarbstoffes und ist dadurch gekenn- zeicIniet, da13 man den =Nlonoazofaihstoff, dcii wau durch saure Kupplung von diano tierter 2-Amino-naphthalin-5-sulfonsäure mit 1-Amiiio-5-oxynaphthalin-7-sulfonsäure erhält,
mit Acetylierungsmitteln behandelt und hier auf den bei dieser Behandlung mitentstan- denen Anteil an N.0-Acetylprodukt durch Einwirkung von Verseifungsmitteln in den Oxyacetylaminoazofarbst.off überführt..
Im nachfolgenden Beispiel bedeuten Teile Gewichtsteile.
Beispiel: 48 Teile des Monoazofarbstoffes, den man durch Vereinigung von dianotierter 2-Amino- naphthalin-5-sulfonsäure mit 1-Amino-5-oxy- naphtlialin-7-sulfonsäure in saurem Medium erhält, werden in einem Gemisch von 200 Tei len Eisessig und 50 Teilen Essigsäureanhy- drid gekocht, bis keine freie Aminogruppe mehr nachweisbar ist.
Nach dem Erkalten wird der abgeschiedene Farbstoff isoliert und durch kurzes Erwärmen in verdünnter Soda lösung die zum Teil acetylierte Hydroxyl- gruppe freigelegt. Hierauf wird ausgesalzen, filtriert und getrocknet. Der so erhaltene Farbstoff, ein dunkles Pulver, färbt Wolle in orangeroten Tönen und kuppelt glatt mit Diazoverbindungen. Seine Lösungsfarbe in konzentrierter Schwefelsäure ist rot, diejenige des Ausgangsfarbstoffes dagegen blau.
Additional patent to main patent No. 262278. Process for the production of an Oxyaeylaminoazofarbatoffes. The present patent relates to a process for the production of a new oxyacetylaminoazo dye and is characterized by the fact that the nlonoazo ingredient is obtained by acidic coupling of dianoated 2-amino-naphthalene-5-sulphonic acid with 1-amino-5 -oxynaphthalene-7-sulfonic acid,
treated with acetylating agents and here converted into the oxyacetylaminoazo dye by the action of saponifying agents on the proportion of N.0-acetyl product that was also formed during this treatment.
In the following example, parts mean parts by weight.
Example: 48 parts of the monoazo dye, which is obtained by combining dianotated 2-amino-naphthalene-5-sulfonic acid with 1-amino-5-oxynaphthalene-7-sulfonic acid in an acidic medium, are mixed with 200 parts of glacial acetic acid and 50 parts of acetic anhydride are boiled until free amino groups can no longer be detected.
After cooling, the deposited dye is isolated and the partially acetylated hydroxyl group is exposed by briefly heating in dilute soda solution. It is then salted out, filtered and dried. The dye thus obtained, a dark powder, dyes wool in orange-red shades and couples smoothly with diazo compounds. Its solution color in concentrated sulfuric acid is red, that of the starting dye is blue.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH262278T | 1946-12-20 | ||
| CH267624T | 1946-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH267624A true CH267624A (en) | 1950-03-31 |
Family
ID=25730561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267624D CH267624A (en) | 1946-12-20 | 1946-12-20 | Process for the preparation of an oxyacylaminoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH267624A (en) |
-
1946
- 1946-12-20 CH CH267624D patent/CH267624A/en unknown
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