DE1644168B2 - - Google Patents
Info
- Publication number
- DE1644168B2 DE1644168B2 DE19511644168 DE1644168A DE1644168B2 DE 1644168 B2 DE1644168 B2 DE 1644168B2 DE 19511644168 DE19511644168 DE 19511644168 DE 1644168 A DE1644168 A DE 1644168A DE 1644168 B2 DE1644168 B2 DE 1644168B2
- Authority
- DE
- Germany
- Prior art keywords
- dye
- superpolyamide
- structures
- dyes
- advantage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000975 dye Substances 0.000 claims description 11
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 claims description 3
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 2
- 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 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 239000004952 Polyamide Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000002657 fibrous material Substances 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920000139 polyethylene terephthalate Polymers 0.000 claims 1
- -1 polyethylene terephthalates Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Es wurde gefunden, daß man einen wertvollen, neuen gelben Dispersionsfarbstoff erhält, wenn man diazotiertes 2,4,5-Trichloranilin mit 2-Phenylindol kuppelt. Die Kupplung der Ausgangskomponenten erfolgt auf an sich bekannte Weise, bevorzugt in saurer wäßriger Lö<m" g oder Suspension bei Temperaturen von 0 bis 10° C. Nach erfolgter Kupplung kann der entstandene farbstoff aus dem Kupplungsgemisch leicht, z. B. durch Filtration abgetrennt werden, da er in Wasser nur wenig löslich ist.It has been found that a valuable new yellow disperse dye is obtained by diazotizing 2,4,5-trichloroaniline couples with 2-phenylindole. The coupling of the starting components takes place on known manner, preferably in acidic aqueous solution or suspension at temperatures from 0 to 10 ° C. After coupling, the resulting dye from the coupling mixture can easily, for. B. separated by filtration, since it is only sparingly soluble in water.
Der erhaltene Farbstoff entspricht der FormelThe dye obtained corresponds to the formula
r\—f V_N==N_C r \ -f V_ N == N_ C
QH5 NQH 5 N
H
und eignet sich sehr gut zum Fäilien und BeH
and is very suitable for filing and loading
196,5 g 2,4,5-Trichloranilin werden in 1000 g Schwefelsäuremonohydrat gelöst und langsam durch Zugabe von 69 g Natriumnitrit diazotiert. Nach halbstündigem Rühren gießt man auf Eis. Zu der so er-196.5 g of 2,4,5-trichloroaniline are dissolved in 1000 g of sulfuric acid monohydrate dissolved and slowly diazotized by adding 69 g of sodium nitrite. After half an hour Stirring is poured onto ice. To the so
jo haltenen Diazolösung fügt man eine Lösung von 194 g 2-Phenylindol in 450 g Schwefelsäure. Nun wird der pH-Wert der Lösung durch Zugabe von Natronlauge oder Natriumacetat auf 1,8 bis 2 erhöht. Nach Beendigung der Reaktion hai sich der Farbstoff in Form von dunklen Kristallen abgeschieden. Es wird abgesaugt, neutral gewaschen und bei 50 bis 600C getrocknet.jo holding diazo solution is added a solution of 194 g of 2-phenylindole in 450 g of sulfuric acid. The pH of the solution is now increased to 1.8 to 2 by adding sodium hydroxide solution or sodium acetate. When the reaction has ended, the dye has deposited in the form of dark crystals. It is suctioned off, washed neutral and dried at 50 to 60 0 C.
In ein Färbebad von 41, O»s 4 g eines emulgierend wirkenden Polyglykoläthers, 0,4 g des gut dispergierten Farbstoffs sowie 16 g eines Carries, beispielsweiseIn a dye bath of 41.0 »s 4 g of an emulsifying agent acting polyglycol ether, 0.4 g of the well-dispersed dye and 16 g of a carry, for example
φ Benzoesäure, und 20 g Diammoniumphosphat enthält, werden 25 g synthetische Superpolyamidfasern bei 500C eingebracht. Man erhitzt innerhalb 30 Minuten zum Kochen und färbt weiter IV2 bis 2 Stunden bei dieser Temperatur. Die Färbung wird anschlie- φ benzoic acid, and contains 20 g of diammonium phosphate, 25 g of synthetic superpolyamide fibers are introduced at 50 ° C. The mixture is heated to the boil over a period of 30 minutes and dyeing continues IV for 2 to 2 hours at this temperature. The coloring is then
p ßend 20 Minuten bei 70° C alkalisch nachgewaschen, gespült und getrocknet. Man erhält eine tiefe klare licht- und waschechte gelbe Färbung. p washed alkaline ßend 20 minutes at 70 ° C, rinsed and dried. A deep, clear, lightfast and washfast yellow coloration is obtained.
Claims (1)
1. Monoazofarbstoff der FormelPatent claims:
1. Monoazo dye of the formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511644168 DE1644168A1 (en) | 1951-01-28 | 1951-01-28 | Process for the preparation of a water-insoluble monoazo dye |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511644168 DE1644168A1 (en) | 1951-01-28 | 1951-01-28 | Process for the preparation of a water-insoluble monoazo dye |
| DEF0049875 | 1966-08-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1644168A1 DE1644168A1 (en) | 1971-02-18 |
| DE1644168B2 true DE1644168B2 (en) | 1974-05-16 |
| DE1644168C3 DE1644168C3 (en) | 1975-01-16 |
Family
ID=25754089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19511644168 Granted DE1644168A1 (en) | 1951-01-28 | 1951-01-28 | Process for the preparation of a water-insoluble monoazo dye |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1644168A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694587A1 (en) | 1994-06-25 | 1996-01-31 | Hoechst Mitsubishi Kasei Co., Ltd. | Monoazoindole dyestuffs |
-
1951
- 1951-01-28 DE DE19511644168 patent/DE1644168A1/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0694587A1 (en) | 1994-06-25 | 1996-01-31 | Hoechst Mitsubishi Kasei Co., Ltd. | Monoazoindole dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1644168A1 (en) | 1971-02-18 |
| DE1644168C3 (en) | 1975-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |