CH308455A - Process for the preparation of a metallizable disazo dye. - Google Patents
Process for the preparation of a metallizable disazo dye.Info
- Publication number
- CH308455A CH308455A CH308455DA CH308455A CH 308455 A CH308455 A CH 308455A CH 308455D A CH308455D A CH 308455DA CH 308455 A CH308455 A CH 308455A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- disazo dye
- dependent
- orange
- metallizable
- 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 8
- 239000000975 dye Substances 0.000 claims description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- -1 aminomonoazo compound Chemical class 0.000 claims description 6
- 229920003043 Cellulose fiber Polymers 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000001530 fumaric 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
- RUCHWTKMOWXHLU-UHFFFAOYSA-N 5-nitroanthranilic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(O)=O RUCHWTKMOWXHLU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 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
- 230000001419 dependent effect Effects 0.000 claims 3
- 239000011230 binding agent Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims 1
- 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-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000003839 salts 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. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines metalli- sierbaren Disazofarbstoffes, welches darin be steht,
dass man 2 Mol der durch Kuppeln von diazoticrter 2-Amino-5-nitrobenzol-l-carbon- säure mit 1-Phenyl-3-methyl-5-pyrazolon-4'- sulfonsäure und nachfolgendes Reduzieren der Nitrogruppe zur Aminogruppe erhält liehen Aminomonoazoverbindung mit 1 Mol eines Fumarsäuredihalogenides umsetzt.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile, und die Prozente sind in Gewichtsprozenten angegeben.
<I>Beispiel:</I> 44,7 Teile der durch Kuppeln von diazo- tierter 2-Amino-5-nitrobenzol-l-carbonsäure mit 1-Phenyl-3-methyl5-pyrazolon-4'-sulfon- säure und nachfolgendes Reduzieren der Nitrogrüppe zur Aminogruppe erhältlichen Aminomonoazoverbindung werden als Dina- triumsalz in 1500 Teilen Wasser gelöst.
Die Lösung wird mit 5 Teilen Lithiumcarbonat und dann bei 5 bis 8 unter gutem Rühren innerhalb von 2 ?/. bis 3 Stunden gleichmässig mit so viel einer 10 1/nigen Lösung von Fumar- säuredichlorid in Chlorbenzol versetzt, bis in. der Kondensationslösung keine freie Amino- gruppe mehr nachweisbar ist. Der so gewon nene Disazofarbstoff wird nach bekannten Methoden isoliert.
Der neue, metallisierbare Disazofarbstoff ist ein orangegelbes Pulver, das sich in kon zentrierter Schwefelsäure und in Wasser mit gelber Farbe löst. Seine gekupferten Färbun gen auf Celiulosefasern sind gelbstichig orange. Die in Substanz hergestellte Kupfer komplexverbindung des Disazofarbstoffes färbt Zellulosefasern ebenfalls in gelbstichig orangen Tönen von ausgezeichneten Licht- und Nassechtheitseigenschaften.
<B> Additional patent </B> to the main patent No. 304388. Process for the production of a metallizable disazo carbate. The subject of the present patent is a process for the production of a metallizable disazo dye, which is
that 2 moles of the aminomonoazo compound borrowed by coupling diazotic 2-amino-5-nitrobenzene-1-carboxylic acid with 1-phenyl-3-methyl-5-pyrazolone-4'-sulfonic acid and then reducing the nitro group to the amino group are obtained 1 mol of a fumaric acid dihalide.
In the example below, parts are parts by weight and percentages are percentages by weight.
<I> Example: </I> 44.7 parts of the acid obtained by coupling diazotized 2-amino-5-nitrobenzene-1-carboxylic acid with 1-phenyl-3-methyl5-pyrazolone-4'-sulfonic acid and the following Reduction of the nitro group to the amino group available amino monoazo compounds are dissolved as dinatrium salt in 1500 parts of water.
The solution is mixed with 5 parts of lithium carbonate and then at 5 to 8 with good stirring within 2? /. For up to 3 hours, enough of a 10 liter solution of fumaric acid dichloride in chlorobenzene was added uniformly until no free amino group can be detected in the condensation solution. The disazo dye thus won is isolated by known methods.
The new, metallizable disazo dye is an orange-yellow powder that dissolves in concentrated sulfuric acid and in water with a yellow color. Its coppered colorations on cellulose fibers are yellowish orange. The copper complex compound of the disazo dye, produced in bulk, also dyes cellulose fibers in yellowish orange tones with excellent light and wet fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308455T | 1952-04-30 | ||
| CH304388T | 1956-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308455A true CH308455A (en) | 1955-07-15 |
Family
ID=25734806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308455D CH308455A (en) | 1952-04-30 | 1952-04-30 | Process for the preparation of a metallizable disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308455A (en) |
-
1952
- 1952-04-30 CH CH308455D patent/CH308455A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH238459A (en) | Process for the preparation of a copper-compatible polyazo dye. | |
| CH308456A (en) | Process for the preparation of a metallizable disazo dye. | |
| CH342310A (en) | Process for the preparation of a substantive disazo dye | |
| CH342316A (en) | Process for the preparation of a substantive disazo dye | |
| CH342309A (en) | Process for the preparation of a substantive disazo dye | |
| CH342311A (en) | Process for the preparation of a substantive disazo dye | |
| CH342315A (en) | Process for the preparation of a substantive disazo dye | |
| CH342313A (en) | Process for the preparation of a substantive disazo dye | |
| AT158260B (en) | Process for the production of azo dyes. | |
| CH342314A (en) | Process for the preparation of a substantive disazo dye | |
| CH342312A (en) | Process for the preparation of a substantive disazo dye | |
| CH307859A (en) | Process for the production of a metallizable polyazo dye. | |
| CH300450A (en) | Process for the preparation of an acidic monoazo dye. | |
| CH308452A (en) | Process for the preparation of a metallizable disazo dye. | |
| CH306238A (en) | Process for the production of a copper-containing azo dye. | |
| CH306241A (en) | Process for the preparation of a substantive disazo dye. | |
| CH308457A (en) | Process for the preparation of a metallizable disazo dye. | |
| CH251393A (en) | Process for the preparation of a new wool azo dye. | |
| CH302037A (en) | Process for the preparation of a chromable disazo dye. | |
| CH306864A (en) | Process for the preparation of a metallizable disazo dye. | |
| CH307177A (en) | Process for the production of a copper-containing azo dye. | |
| CH297411A (en) | Process for the preparation of an acidic monoazo dye. | |
| CH242844A (en) | Process for the preparation of a chromable monoazo dye. | |
| CH308461A (en) | Process for the preparation of a metallizable disazo dye. | |
| CH307170A (en) | Process for the production of a copperable azo dye. |