CH308458A - Process for the preparation of a metallizable disazo dye. - Google Patents
Process for the preparation of a metallizable disazo dye.Info
- Publication number
- CH308458A CH308458A CH308458DA CH308458A CH 308458 A CH308458 A CH 308458A CH 308458D A CH308458D A CH 308458DA CH 308458 A CH308458 A CH 308458A
- Authority
- CH
- Switzerland
- Prior art keywords
- disazo dye
- acid
- dependent
- metallizable
- maleic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 7
- 239000000975 dye Substances 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- -1 aminomonoazo compound Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ZLYYJUJDFKGVKB-UPHRSURJSA-N (z)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C/C(Cl)=O ZLYYJUJDFKGVKB-UPHRSURJSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000003756 stirring Methods 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
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/145—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with polycarboxylic acids
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 304388. Verfahren zur Herstellung eines metallisierbaren Disazofarbatoffes.N Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines metalli- sierbaren Disazofarbstaffes, welches darin be steht, dass man 2 Mol der durch Kuppeln von diazotierter 2-Amino-l-carboxybenzol-5-sulfon- säure mit 1- (4'-Amino)
- phenyl - 3 - methyl-5- pyrazolon erhältlichen Aminomonoazoverbin- dung mit 1 Mol eines Maleinsäuredihalogenides umsetzt.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile, und die Prozente sind in Gewichtsprozenten angegeben.
<I>Beispiel:</I> 41,7 Teile der durch Kuppeln von diazo- tierter 2-Amino-l-carboxybenzol-5-sulfonsäure mit 1-(4'-Amino)-phenyl-3-methyl-5-pyra.zolon erhältlichen Aminomonoazoverbindung werden mittels der hierzu notwendigen Menge Na- triumearbonat in 2500 Teilen Wasser gelöst.
In die Lösung tropft man unter gutem Rüh ren innerhalb von 4-5 Stunden so viel einer 10o/oigen Lösung von Maleinsäuredichlorid in Chlorbenzol, bis sich darin keine freie Amino- gruppe mehr nachweisen lässt. Bei dieser Ope ration wird durch gleichzeitiges Zutropfen von 5 % iger Natriumcarbonatlösung der pH- Wert der Reaktionslösung zwischen 6,0 und 8,0 gehalten.
Hierauf wird der gebildete Dis a7ofarbstoff nach den üblichen Methoden ab geschieden, abfiltriert und getrocknet.
Der neue, metallisierbare Disazofarbstoff ist ein orangebraunes Pulver, welches sich in konzentrierter Schwefelsäure und in Wasser mit gelber Farbe löst und Baumwolle und Fa sern aus regenerierter Cellulose in gelben Tönen färbt. Die Färbungen des neuen Dis- azofarbstoffes besitzen, besonders wenn sie mit kupferabgebenden Mitteln nachbehandelt werden, ausgezeichnete Licht- und Nassecht- heitseigenschaften.
<B> Additional patent </B> to the main patent no. 304388. Process for the production of a metallizable disazo carbate.N The subject of the present patent is a process for the production of a metallizable disazo dye, which consists in that 2 mol of the by coupling of diazotized 2-amino-l-carboxybenzene-5-sulfonic acid with 1- (4'-amino)
- phenyl - 3 - methyl-5-pyrazolone available aminomonoazo compound with 1 mol of a maleic acid dihalide.
In the following example, parts are parts by weight and percentages are percentages by weight.
<I> Example: </I> 41.7 parts of the compound obtained by coupling diazotized 2-amino-1-carboxybenzene-5-sulfonic acid with 1- (4'-amino) -phenyl-3-methyl-5-pyra Aminomonoazo compounds obtainable zolon are dissolved in 2500 parts of water using the amount of sodium carbonate required for this.
While stirring well, enough of a 10% solution of maleic acid dichloride in chlorobenzene is added dropwise to the solution within 4-5 hours until no free amino group can be detected any longer. During this operation, the pH of the reaction solution is kept between 6.0 and 8.0 by simultaneous dropwise addition of 5% sodium carbonate solution.
The dis a7o dye formed is then separated off, filtered off and dried according to the usual methods.
The new, metallizable disazo dye is an orange-brown powder which dissolves in concentrated sulfuric acid and water with a yellow color and dyes cotton and fibers made from regenerated cellulose in yellow tones. The colorations of the new disazo dye have excellent light and wet fastness properties, especially when they are aftertreated with copper-releasing agents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308458T | 1952-04-30 | ||
| CH304388T | 1956-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308458A true CH308458A (en) | 1955-07-15 |
Family
ID=25734809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308458D CH308458A (en) | 1952-04-30 | 1952-04-30 | Process for the preparation of a metallizable disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308458A (en) |
-
1952
- 1952-04-30 CH CH308458D patent/CH308458A/en unknown
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