CH308465A - Process for the preparation of a copper-containing disazo dye. - Google Patents
Process for the preparation of a copper-containing disazo dye.Info
- Publication number
- CH308465A CH308465A CH308465DA CH308465A CH 308465 A CH308465 A CH 308465A CH 308465D A CH308465D A CH 308465DA CH 308465 A CH308465 A CH 308465A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- acid
- disazo dye
- amino group
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 9
- 229910052802 copper Inorganic materials 0.000 title claims description 9
- 239000010949 copper Substances 0.000 title claims description 9
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 11
- -1 aminomonoazo compound Chemical class 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 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 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003795 chemical substances by application 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
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007747 plating Methods 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FBAQFBBASACECK-UHFFFAOYSA-N 2-amino-6-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound NC1=CC=CC(C=CC=2C(=CC=CC=2)S(O)(=O)=O)=C1S(O)(=O)=O FBAQFBBASACECK-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 304388. Verfahren zur Herstellung eines kupferhaltigen Disazofarbstoffes. Clegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines kupfer- lialtigen Disazofarbstoffes, welches darin be steht, dass man 2 Mol der Amillomonoazover- bindung,
die erhalten wird durch Kuppeln von diazotierter 2-Amino-l-carboxybenzol-5- sulfonsäure m.it 4-Acetoacetylamino-4'-carb- ätlioxy aminostilben - 2,2'- disulfonsäure und ;lachfolgendes Verseifen der Carbäthoxy- aminogruppe mir Aminogruppe, mit 1 Mol eines Fumarsäuredihalogenides umsetzt und den erhaltenen Disazofarbstoff mit, kupfer abgebenden Mitteln behandelt.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile, und die Prozente sind in Cxewichtsprozenten angegeben.
<I>Beispiel:</I> 84;2 Teile der durch Kuppeln von diazo- tierter 2-Amino-1-carboxybenzol-5-sulfonsäure mit 4-Acetoacet.jamino-4'-carbäthoxyamino- stilben-2,2'-distilfonsäure erhaltenen IMonoazo- verbindung werden als'Tetranatriumsalz in 2000 Teile 3 o/oige Natriumhydroxydlösung gebracht und bei einer Temperatur von 80-90 wäh rend 1 Stunde gerührt,
wodurch die C'arb- äthoxyaminogruppe der Monoazoverbindung zur Aminogruppe verseift wird. Die Lösung wird auf 5 -10 gekühlt und bei dieser Tem peratur unter gutem Rühren innerhalb von i 7. - 2 'Stunden mit so viel einer 20 o/oigen Lösung von Fumarsäuredichlorid in Chlor benzol versetzt, bis darin keine freie Amino- gruppe mehr nachweisbar ist. Hierauf wird der gebildete Disazofarbstoff auf bekannte Weise isoliert.
Der in konzentrierter Schwefel säure mit gelber Farbe lösliche Farbstoff wird nach bekannten Methoden mit kupferabgeben den Mitteln behandelt.
Der neue, kupferhaltige Disazofarbstoff färbt Baumwolle und Fasern aus regenerier ter Cellulose in grünstiehig gelben Tönen von geiten Licht- und Nassechtheitseigenschaften. In ebensolehen Tönen sind die nach dem Nachkupferungsverfahren hergestellten Fär bungen gehalten.
Additional patent to main patent No. 304388. Process for the production of a copper-containing disazo dye. The status of the present patent is a process for the preparation of a copper-lialtigen disazo dye, which consists in adding 2 moles of the amillomonoazo compound,
which is obtained by coupling diazotized 2-amino-l-carboxybenzene-5-sulfonic acid with 4-acetoacetylamino-4'-carb-ätlioxy aminostilben-2,2'-disulfonic acid and; subsequent saponification of the carbethoxy amino group with amino group, reacted with 1 mol of a fumaric acid dihalide and treated the disazo dye obtained with copper-releasing agents.
In the following example, the parts are parts by weight and the percentages are given in percent by weight.
<I> Example: </I> 84; 2 parts of the compound obtained by coupling diazo- tated 2-amino-1-carboxybenzene-5-sulfonic acid with 4-acetoacet.jamino-4'-carbethoxyamino-stilbene-2,2'- The monoazo compound obtained from distilfonic acid is brought as a tetra sodium salt into 2000 parts of 3% sodium hydroxide solution and stirred at a temperature of 80-90 for 1 hour,
whereby the C'arb- ethoxyamino group of the monoazo compound is saponified to the amino group. The solution is cooled to 5-10 and at this temperature, with thorough stirring, enough of a 20% solution of fumaric acid dichloride in chlorobenzene is added in the course of 1.7-2 hours until no free amino group can be detected is. The disazo dye formed is then isolated in a known manner.
The dye, which is soluble in concentrated sulfuric acid with a yellow color, is treated according to known methods with copper-releasing agents.
The new, copper-containing disazo dye dyes cotton and fibers made from regenerated cellulose in greenish yellow tones with good light and wet fastness properties. The colors produced by the copper plating process are kept in just the same tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308465T | 1952-04-30 | ||
| CH304388T | 1956-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308465A true CH308465A (en) | 1955-07-15 |
Family
ID=25734816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308465D CH308465A (en) | 1952-04-30 | 1952-04-30 | Process for the preparation of a copper-containing disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308465A (en) |
-
1952
- 1952-04-30 CH CH308465D patent/CH308465A/en unknown
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