CH308452A - Process for the preparation of a metallizable disazo dye. - Google Patents
Process for the preparation of a metallizable disazo dye.Info
- Publication number
- CH308452A CH308452A CH308452DA CH308452A CH 308452 A CH308452 A CH 308452A CH 308452D A CH308452D A CH 308452DA CH 308452 A CH308452 A CH 308452A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- acid
- coupling
- dependent
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title 1
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 239000000987 azo dye Substances 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 0.000 claims description 3
- 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
- -1 amino monoazo compound Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 239000000975 dye Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 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
- ZYDILTJZICMURJ-UHFFFAOYSA-N 1-(2,3-diaminophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N)=C1N ZYDILTJZICMURJ-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000004627 regenerated cellulose Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 2
- 238000010367 cloning Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 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
-
- 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
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
- C09B45/42—Copper compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 304388. Verfahren zur Herstellung eines metallisierbaren Azofarbstoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines metalli- sierbaren Azofarbstoffes, welches darin be steht, dass man 1 Mol der Aminodisazoverbin- clung,
die erhalten wird durch Kuppeln von diazotierter 2-Amino-5-nitrobenzol-l-carbon- säure mit 1-Phenyl-3-methyl-5-pyrazolon-4'- sulfonsäure, nachfolgendes Reduzieren der 1Vitrogruppe zur Aminogruppe, Diazotieren der nun vorliegenden Aminomonoazoverbin- clung und Kuppeln mit 1-Amino-3-methyl- benzol,
und 1 Mol der -durch Kuppeln von dianotierter 4-Amino-2-carboxy-l-oxybenzol-6- sulfonsäu,re mit 1-Amino-3-acetylaminobenzol hergestellten Aminomonoazoverbindung mit 1 Mol eines Fumarsäuredihalogenides um setzt.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile.
<I>Beispiel:</I> 26,8 Teile (= 0,05 Mol) der Aminodisazo- Verbindung, die erhalten wird durch Kuppeln von diazotierter 2-Amino-5-nitrobenzol-l-car- bonsäure mit 1-Phenyl-3-methyl-5-pyrazolon- 4'-sulfonsäure, nachfolgendes Reduzieren der Nitrogruppe zur Aminogruppe, Diazotieren der nun vorliegenden Aminomonoa.zoverbin- dung und Kuppeln mit 1-Amino-3-methyl- benzol und 19,7 Teile (= 0,
05 Mol) der durch ,Kuppeln von dianotierter 4-Amino 2-ca.rboxy- 1-oxybenzol-6-sulfonsäure mit 1-Amino-3- aeetylaminobenzol hergestellten Aminomono- azoverbindungen werden zusammen in 3000 Teilen Wasser unter Zusatz von Natrium hydroxyd gelöst.
In die Lösung tropft man unter gutem Rühren eine Mischung aus 7,7 Teilen Fumar- säuredichlorid und 8 Teilen Benzol und gleichzeitig so viel .einer konzentrierten Na- triumearbonatlösung, dass die Reaktion der Kondensationslösung schwach alkalisch bleibt. Nachdem man alles Fumarsäuredichlorid ein getragen hat, wird die Kondensationslösung weitergerührt, bis sich darin keine freie Aminogruppe mehr nachweisen lässt.
Hierauf wird der gebildete Azofarbstoff in der Wärme mit Hilfe von Natriumchlorid ab geschieden, abfiltriert und getrocknet.
Der neue, metallisierbare Azofarbstoff ist ein gelbbraunes Pulver, welches sich in Wasser mit gelber, in konzentrierter Schwe felsäure mit bordeauxroter Farbe löst und Baumwolle und Fasern aus regenerierter Celhilose in lichtechten orangen Tönen färbt, die durch Nachbehandeln mit kupferabgeben den Mitteln noch nassechter werden.
Additional patent to main patent No. 304388. Process for the production of a metallizable azo dye. The subject of the present patent is a process for the preparation of a metallizable azo dye, which consists in adding 1 mol of the aminodisazo compound,
which is obtained by coupling diazotized 2-amino-5-nitrobenzene-1-carboxylic acid with 1-phenyl-3-methyl-5-pyrazolone-4'-sulfonic acid, subsequent reduction of the 1-nitro group to the amino group, diazotization of the aminomonoazo-compound now present - Cloning and coupling with 1-amino-3-methylbenzene,
and 1 mol of the aminomonoazo compound prepared by coupling dianotated 4-amino-2-carboxy-1-oxybenzene-6-sulfonic acid with 1-amino-3-acetylaminobenzene with 1 mol of a fumaric acid dihalide.
In the following example, the parts are parts by weight.
<I> Example: </I> 26.8 parts (= 0.05 mol) of the aminodisazo compound, which is obtained by coupling diazotized 2-amino-5-nitrobenzene-1-carboxylic acid with 1-phenyl- 3-methyl-5-pyrazolone-4'-sulfonic acid, subsequent reduction of the nitro group to the amino group, diazotization of the aminomonoa.zo compound now present and coupling with 1-amino-3-methylbenzene and 19.7 parts (= 0,
05 mol) of the aminomono- azo compounds produced by coupling dianotated 4-amino-2-ca-rboxy-1-oxybenzene-6-sulfonic acid with 1-amino-3-acetylaminobenzene are dissolved together in 3000 parts of water with the addition of sodium hydroxide.
A mixture of 7.7 parts of fumaric acid dichloride and 8 parts of benzene and at the same time so much of a concentrated sodium carbonate solution that the reaction of the condensation solution remains weakly alkaline is added dropwise to the solution with thorough stirring. After all the fumaric acid dichloride has been introduced, the condensation solution is stirred further until no free amino group can be detected in it.
The azo dye formed is then separated off in the heat with the aid of sodium chloride, filtered off and dried.
The new, metallizable azo dye is a yellow-brown powder that dissolves in water with yellow, in concentrated sulfuric acid with a burgundy red color and dyes cotton and fibers from regenerated celhilose in lightfast orange tones, which are made even more wet-fast by post-treatment with copper-releasing agents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308452T | 1952-04-30 | ||
| CH304388T | 1956-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308452A true CH308452A (en) | 1955-07-15 |
Family
ID=25734803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308452D CH308452A (en) | 1952-04-30 | 1952-04-30 | Process for the preparation of a metallizable disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308452A (en) |
-
1952
- 1952-04-30 CH CH308452D patent/CH308452A/en unknown
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