CH449143A - Process for the preparation of new monoazo dyes - Google Patents
Process for the preparation of new monoazo dyesInfo
- Publication number
- CH449143A CH449143A CH588465A CH588465A CH449143A CH 449143 A CH449143 A CH 449143A CH 588465 A CH588465 A CH 588465A CH 588465 A CH588465 A CH 588465A CH 449143 A CH449143 A CH 449143A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- monoazo dyes
- parts
- formula
- dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 aminomonoazo Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical group CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004043 dyeing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 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 1
- 239000004952 Polyamide Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung neuer Monoazofarbstoffe Die Erfindung bezieht sich auf ein Verfahren zur Herstellung wertvoller, neuer Monoazofarbstoffe der Formel
EMI0001.0006
worin ein X und ein Y je ein Wasserstoffatom und das andere X bzw. Y je eine Sulfonsäuregruppe und n eine ganze positive Zahl bedeuten.
Das Verfahren ist dadurch gekennzeichnet, dass man ein 2,4,6-Trihalogen@-1,3,5-triazin wie Cyanur- chlorid im Moleverhältnis von ca. 1:1 einerseits mit einem N-Alkylanilin wie N-@Methyl- oder N Ä.thylanilin und andererseits mit einem Aminomonoazofarbstoff der Formel
EMI0001.0019
in beliebiger Reihenfolge kondensiert. Diese Umsetzun gen können nach an sich bekannten Methoden, z.
B. in wässrigem Medium in Gegenwart säurebindender Mit tel, wie Alkaliacetate, -carbonate oder -hydroxyde erfolgen.
Die nach vorliegendem Verfahren erhaltenen Farb- stoffe der Formel (1) sind neu. Sie eignen sich zum Färben und Bedrucken der verschiedensten Materi alien, z. B. solcher tierischer Herkunft wie Seide und vor allem Wolle sowie verschiedene Kunstfasern, z. B.
animalismerte Kunstseide, Superpolyamiden und Super- polyurethanen insbesondere aber polyhydroxylierter Materialien faseriger Struktur, wie Zellstoff, regene- rierte Cellulose oder Viscose, Leinen oder vor allem Baumwolle.
Sie eignen sich besonders zur Herstellung von zum Färben, Foulardieren oder auch zum Drucken verwendbaren, salzhaltigen, wässrigen Farbstofflösun- gen. Die durch Foulardieren, Drucken oder Direktfär ben auf die Faser aufgebrachten, erfindungsgemässen Farbstoffe können zwecks Fixierung einer Wärmebe handlung in Gegenwart von Alkali, z. B. in Gegenwart von Natriumcarbonat, Natriumhydroxyd, Erdalkali- hydroxyden, Trinatriumphosphat usw. unterworfen werden. Die Färbung kann z.
B. bei erhöhter bis, mäs- sig erhöhter Temperatur, d. h. 50 bis 100 , ausgeführt werden. Zwecks Ausschöpfung des Bades ist es emp fehlenswert, gleichzeitig mit den Farbstoffen oder wäh rend des Färbeprozesses mehr oder weniger neutrale, vor allem anorganische Salze wie Alkalichloride oder Sulfate gegebenenfalls portionenweise dem Färbebad zuzusetzen. In den meisten Fällen kann es von Vorteil sein, die mit den vorliegenden Farbstoffen nach den Foulardierverfahren,
für die sie im Hinblick auf Ihre günstigen Löslichkeits- und Elektrolytempfindlichkeits- Verhältnisse, sowie der guten Stabilität deren Druckpa sten, ganz besonders geeignet sind, erhältlichen Fär bungen einer Nachbehandlung zu unterwerfen. So wer den z. B. die erhaltenen Färbungen zweckmässig abge seift; durch diese Nachbehandlung werden die nicht vollständig fixierten Farbstoffanteile entfernt.
Im Beispiel bedeuten die Teile, sofern nichts am derer erwähnt wird, Gewichtsteile, die Prozente Ge wichtsprozente, und die Temperaturen sind in Celsius, graden angegeben. Zwischen Gewichts- und Volumen teilen besteht das gleiche Verhältnis wie zwischen einem Gramm und einem Milliliter. <I>Beispiel</I> Zu einer eisgekühlten, wässrigen Lösung von 63,5 Teilen des Natriumsalzes des 1-Amino-3,6-disulfo- 7-(1'-sulfo-3'-carboxyphenylazo)-8-naphthols (erhalten durch Kuppeln von diazotierter 2-Amino-5-sulfoben- zoesäure mit 1-Amino-8-oxynaphthalin 3,6-disulfonsäure in alkalischer Lösung)
wird eine Lösung von 18,5 Teilen Cyanurchlorid in 50 Teile Aceton zugeben. Das Gemisch wird zwischen 0 und. 5 gerührt, wobei durch Zutropfen einer verdünnten Natriumhydroxydlösung die Reaktion neutral gehalten wird. Wenn keine Aminogruppe mehr nachweisbar ist, werden 10,7 Teile N-Methylannhn zu gegeben.
Das Gemisch wird dann 2 Stunden bei 30 ge- rührt und mit einer Natriumhydroxydlösung neutralisiert. Der Farbstoff wird durch Aussahen und Trocknen iso- liert.
Er färbt Baumwolle in blaustichig roten Tönen. Thermo f <I>fixier f</I> ärbeverf ahren: 3 Teile des gemäss Beispiel erhaltenen Farbstoffes und 2 Teile Natriumcarbonat werden; in; 25 Teilen Harnstoff und 75 Teilen Wasser gelöst. Mit dieser Lösung imprägniert man ein Baumwollgewebe, quetscht auf 75 % Gewichtszunahme ab und trocknet bei 80 .
Dann unterwirft man den Stoff einer trockenen Hitze von 140 während 6 Minuten, spült und seift bei Kochtemperatur. Es resultiert eine kochechte Färbung.
Process for the preparation of new monoazo dyes The invention relates to a process for the preparation of valuable, new monoazo dyes of the formula
EMI0001.0006
wherein one X and one Y are each a hydrogen atom and the other X or Y is each a sulfonic acid group and n is an integer positive number.
The process is characterized in that a 2,4,6-trihalogen @ -1,3,5-triazine such as cyanuric chloride in a molar ratio of about 1: 1 on the one hand with an N-alkylaniline such as N- @ methyl or N Ä.thylanilin and on the other hand with an amino monoazo dye of the formula
EMI0001.0019
condensed in any order. This Umsetzun conditions can according to known methods, for.
B. in an aqueous medium in the presence of acid-binding means with tel, such as alkali acetates, carbonates or hydroxides.
The dyes of the formula (1) obtained by the present process are new. They are suitable for dyeing and printing a wide variety of materi alien, z. B. of animal origin such as silk and especially wool and various synthetic fibers such. B.
Animalized rayon, super polyamides and super polyurethanes, but especially polyhydroxylated materials with a fibrous structure, such as cellulose, regenerated cellulose or viscose, linen or especially cotton.
They are particularly suitable for the production of saline, aqueous dye solutions that can be used for dyeing, padding or printing. z. B. in the presence of sodium carbonate, sodium hydroxide, alkaline earth hydroxides, trisodium phosphate, etc. are subjected. The coloring can e.g.
B. at elevated to moderately elevated temperature, d. H. 50 to 100. In order to exhaust the bath, it is recommended to add more or less neutral, especially inorganic salts such as alkali chlorides or sulfates to the dyebath at the same time as the dyes or during the dyeing process. In most cases, it can be advantageous to use the dyes present in the padding process,
for which they are particularly suitable in view of their favorable solubility and electrolyte sensitivity ratios, as well as the good stability of their Druckpa most, to subject available dyeings to an aftertreatment. So who the z. B. appropriately soaps the dyeings obtained; this post-treatment removes the not completely fixed dye components.
In the example, the parts, unless otherwise stated, are parts by weight, the percentages are percentages by weight and the temperatures are given in degrees Celsius. The relationship between weight and volume is the same as that between a gram and a milliliter. <I> Example </I> To an ice-cold, aqueous solution of 63.5 parts of the sodium salt of 1-amino-3,6-disulfo-7- (1'-sulfo-3'-carboxyphenylazo) -8-naphthol ( obtained by coupling diazotized 2-amino-5-sulfobenzoic acid with 1-amino-8-oxynaphthalene 3,6-disulfonic acid in alkaline solution)
a solution of 18.5 parts of cyanuric chloride in 50 parts of acetone is added. The mixture will be between 0 and. 5 stirred, the reaction being kept neutral by adding a dilute sodium hydroxide solution dropwise. When no more amino group can be detected, 10.7 parts of N-methylannhn are added.
The mixture is then stirred at 30 for 2 hours and neutralized with a sodium hydroxide solution. The dye is isolated by looking and drying.
It dyes cotton in bluish red tones. Thermal fixation process: 3 parts of the dye obtained according to the example and 2 parts of sodium carbonate are used; in; Dissolved 25 parts of urea and 75 parts of water. A cotton fabric is impregnated with this solution, squeezed to a 75% weight gain and dried at 80.
The fabric is then subjected to a dry heat of 140 for 6 minutes, rinsed and soaped at boiling temperature. The result is a boil-fast color.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH588465A CH449143A (en) | 1961-03-08 | 1961-03-08 | Process for the preparation of new monoazo dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH588465A CH449143A (en) | 1961-03-08 | 1961-03-08 | Process for the preparation of new monoazo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH449143A true CH449143A (en) | 1967-12-31 |
Family
ID=4300931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH588465A CH449143A (en) | 1961-03-08 | 1961-03-08 | Process for the preparation of new monoazo dyes |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH449143A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0668327A1 (en) * | 1994-02-11 | 1995-08-23 | Hoechst Aktiengesellschaft | Water-soluble azo compounds, process for their preparation and their use as dyestuffs |
-
1961
- 1961-03-08 CH CH588465A patent/CH449143A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0668327A1 (en) * | 1994-02-11 | 1995-08-23 | Hoechst Aktiengesellschaft | Water-soluble azo compounds, process for their preparation and their use as dyestuffs |
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