CH290493A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH290493A CH290493A CH290493DA CH290493A CH 290493 A CH290493 A CH 290493A CH 290493D A CH290493D A CH 290493DA CH 290493 A CH290493 A CH 290493A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkaline
- coupling
- medium
- acid
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000987 azo dye Substances 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007747 plating Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- XEHOHEOLJRJJAS-UHFFFAOYSA-N CC(CC(NC1=CC=C(C=CC(C(S(O)(=O)=O)=C2)=CC=C2NC(CC(C)=O)=O)C(S(O)(=O)=O)=C1)=O)=O Chemical compound CC(CC(NC1=CC=C(C=CC(C(S(O)(=O)=O)=C2)=CC=C2NC(CC(C)=O)=O)C(S(O)(=O)=O)=C1)=O)=O XEHOHEOLJRJJAS-UHFFFAOYSA-N 0.000 claims 1
- FROLMIGPHKATQS-UHFFFAOYSA-N 2-amino-5-benzamidobenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1NC(=O)C1=CC=CC=C1 FROLMIGPHKATQS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 286113. Verfahren zur Herstellung eines Azofarbstofes. Es wurde gefunden, dass man zu einem neuen Azofarbstoff gelangt, wenn man 4,4' Di- (acetöacetylamino) -stüben-2,
2'-disulfon- säure auf der einen Seite mit diazotierter 2-Amino-5-benzoylaminobenzol-1-carbonsäure und auf der andern mit diazotierter 2-Amino- 5-chlorbenzol-l-carbonsäure kuppelt.
Der neue Farbstoff bildet ein gelbes Pul ver, das sich in Wasser und in konzentrierter Schwefelsäure mit gelber Farbe löst und das Baumwolle nach dem ein- oder zweibadigen Nachkupferungsverfahren in echten, grün stichig gelben Tönen färbt.
Die Kupplungsreaktionen können in belie biger Reihenfolge durchgeführt werden. Man lässt zum Beispiel die erste Kupplung in essig saurem bis alkalibicarbonatalkalischem Me dium vor sieh gehen. Zweckmässig wird sie in essigsaurem Medium begonnen und in al- kalibicarbonatalkalischem Medium beendet. Die zweite Kupplung führt man vorteilhaft in alkalischem, vorzugsweise in alkalicarbo- natalkalischem, Medium durch.
<I>Beispiel:</I> 5,1 Teile 2-Amino-5-benzoylaminobenzol-l- carbonsäure werden in bekannter Weise mit 1,4 Teilen Natriumnitrit diazotiert und unter Kühlung in essigsaurem Mittel mit 10,6 Teilen 4,4' - Di-acetoacetylaminostilben- 2,2'- disulfon- säure gekuppelt. Die Kupplung kann durch Zutropfen von Natriumbicarbonatlösung be schleunigt werden.
Hernach vereinigt man in natriumearbonatalkalischer Lösung mit der aus 3,4 Teilen 2-Amino-5-chlorbenzol-l-car- bonsäure erhaltenen Diazoverbindung. Nach beendeter Kupplung wird der Farbstoff ab filtriert und getrocknet.
<B> Additional patent </B> to main patent no. 286113. Process for the production of an azo dye. It has been found that a new azo dye is obtained if 4,4 'di- (acetöacetylamino) -stüben-2,
2'-disulfonic acid on one side with diazotized 2-amino-5-benzoylaminobenzene-1-carboxylic acid and on the other with diazotized 2-amino-5-chlorobenzene-1-carboxylic acid.
The new dye forms a yellow powder that dissolves in water and concentrated sulfuric acid with a yellow color and colors the cotton in real, green-tinged yellow shades using the one- or two-bath post-copper plating process.
The coupling reactions can be carried out in any order. For example, the first coupling is allowed to proceed in acetic acid to alkali bicarbonate-alkaline medium. It is expedient to start it in an acetic acid medium and to end it in an alkaline bicarbonate-alkaline medium. The second coupling is advantageously carried out in an alkaline medium, preferably in an alkaline carbonate-alkaline medium.
<I> Example: </I> 5.1 parts of 2-amino-5-benzoylaminobenzene-1-carboxylic acid are diazotized in a known manner with 1.4 parts of sodium nitrite and, with cooling in an acetic acid agent, with 10.6 parts of 4.4 ' - Di-acetoacetylaminostilbene-2,2'-disulfonic acid coupled. The coupling can be accelerated by adding dropwise sodium bicarbonate solution.
Then it is combined in an alkaline sodium carbonate solution with the diazo compound obtained from 3.4 parts of 2-amino-5-chlorobenzene-1-carboxylic acid. After coupling has ended, the dye is filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH286113T | 1950-03-17 | ||
| CH290493T | 1951-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH290493A true CH290493A (en) | 1953-04-30 |
Family
ID=25732574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH290493D CH290493A (en) | 1950-03-17 | 1951-01-31 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH290493A (en) |
-
1951
- 1951-01-31 CH CH290493D patent/CH290493A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH290493A (en) | Process for the preparation of an azo dye. | |
| CH290495A (en) | Process for the preparation of an azo dye. | |
| CH290494A (en) | Process for the preparation of an azo dye. | |
| CH258758A (en) | Process for the preparation of an azo dye. | |
| CH265720A (en) | Process for the preparation of a copper-compatible polyazo dye. | |
| CH282258A (en) | Process for the preparation of a monoazo dye. | |
| CH202743A (en) | Process for the preparation of an azo dye. | |
| CH202749A (en) | Process for the preparation of an azo dye. | |
| CH202747A (en) | Process for the preparation of an azo dye. | |
| CH261058A (en) | Process for the preparation of a polyazo dye. | |
| CH202746A (en) | Process for the preparation of an azo dye. | |
| CH285140A (en) | Process for the preparation of a disazo dye. | |
| CH220751A (en) | Process for the production of a new azo dye. | |
| CH302038A (en) | Process for the preparation of a chromable disazo dye. | |
| CH237130A (en) | Process for the production of a new azo dye. | |
| CH261066A (en) | Process for the preparation of a polyazo dye. | |
| CH202750A (en) | Process for the preparation of an azo dye. | |
| CH282261A (en) | Process for the preparation of a monoazo dye. | |
| CH301816A (en) | Process for the preparation of a monoazo dye. | |
| CH286113A (en) | Process for the preparation of an azo dye. | |
| CH202748A (en) | Process for the preparation of an azo dye. | |
| CH267309A (en) | Process for the preparation of an azo dye. | |
| CH308456A (en) | Process for the preparation of a metallizable disazo dye. | |
| CH273306A (en) | Process for the preparation of an azo dye. | |
| CH265723A (en) | Process for the preparation of a copper-compatible polyazo dye. |