CH310699A - Process for the preparation of an anthraquinone naphthocarbazole dye. - Google Patents
Process for the preparation of an anthraquinone naphthocarbazole dye.Info
- Publication number
- CH310699A CH310699A CH310699DA CH310699A CH 310699 A CH310699 A CH 310699A CH 310699D A CH310699D A CH 310699DA CH 310699 A CH310699 A CH 310699A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- anthraquinone
- water
- acid
- naphthocarbazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- IYBVUAUERRIYRH-UHFFFAOYSA-N C1=C2C=CC3=C(C=CC=4C=5C=CC=CC5NC34)C2=CC=C1.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O Chemical compound C1=C2C=CC3=C(C=CC=4C=5C=CC=CC5NC34)C2=CC=C1.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O IYBVUAUERRIYRH-UHFFFAOYSA-N 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- -1 carbonation Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000009963 fulling Methods 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 239000013535 sea water Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000004552 water soluble powder Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000000980 acid dye Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YUIJPNGDODVPKK-UHFFFAOYSA-N 1-(naphthalen-2-ylamino)anthracene-9,10-dione Chemical compound C1=C(C=CC2=CC=CC=C12)NC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O YUIJPNGDODVPKK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 210000004243 sweat 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/26—Carbazoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 303287. Verfahren zur Herstellung eines Anthrachinon-naphthocarbazol-Farbstoffes. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines An thrachinon-naphthocarbazol-Farbstoffes, wel ches dadurch gekennzeichnet ist, dass man 1- [ p - (Phenylsulfonyl)
- benzainido ] - 2 - methyl-4- Das erhaltene Carbazol von der Formel
EMI0001.0011
ist in Form eines Natriumsalzes ein wasser lösliches Pulver, das Wolle aus neutralem oder saurem Farbbad in tief rötlichbraunen Tönen färbt, wobei die Färbung eine ausgezeichnete Licht-, Walk-, Chlor-, Reibiungs-, Schweiss-, Meerwasser-, Carbonierungs-, Wasserflecken-, Säure- und. Alkaliflecken- und Hitzeechtheit aufweist.
Beispiel.: 5 Gewichtsteile 1- [p- (Phenylsulfonyl)- benza.mido] -2-methyl-4- (2-naphthylamino)- anthrachinon (violettes Pulver vom Schmelz punkt 249 C nach Umkristallisieren aus o- Dichlorbenzol) wurden in 23 Gewichtsteile 100o/oiger Schwefelsäure eingerührt und das (2-naphthylamino)-anthrachinon mit einem Sulfoniertungsmittel behandelt, derart,
dass Carbazolringschluss erfolgt und eine Sulfo- gruppe in den Naphthalinkern eingeführt wird. Reaktionsgemisch wurde bei 40 C etwa 4 Stunden dang gerührt, um den Carbazolring schluss und die Sulfonierung zu vervollständi gen.
Die Mischung wurde dann in etwa 250 Teile einer eiskalten, 4o/oigen wässerigen Na- triumsulfatlösung gegossen und der gebildete Niederschlag abfiltriert und mit einer gerin gen Menge kalter, 4o/o.iger wässeriger Na: triumsulfatlösung gewaschen. Der Filter kuchen wurde in Wasser aufgeschlämmt, mit Natriumcarbonat neutralisiert und die ent standene Lösung zur Trockne verdampft, wo bei das Carbazol erhalten wurde.
Das erhaltene Carbazol ist in Form des Natriumsalzes ein wasserlösliches Pulver, das Wolle aus neutralem oder saurem Farbbad in tief rötlichbraunen Tönen färbt, die etwas gel ber und dunkler sind als die mit dem Farb stoff nach dem Hauptpatent erzeugten.
Die mit dem Farbstoff erhaltenen Färbun gen weisen eine ausgezeichnete Licht-, Wasch-, Walk-, Chlor-, Reibungs , Schweiss-, Meer wasser-, Carbonierungs-, Wasserflecken-, Säure- und Alkaliflecken- und Hitzeechtheit auf.
Der erhaltene Farbstoff hat die Formel
EMI0002.0008
Additional patent to main patent No. 303287. Process for the production of an anthraquinone-naphthocarbazole dye. The present invention relates to a process for the preparation of an anthrachinone-naphthocarbazole dye, which is characterized in that 1- [p - (phenylsulfonyl)
- benzainido] - 2 - methyl-4- The obtained carbazole of the formula
EMI0001.0011
is a water-soluble powder in the form of a sodium salt that dyes wool from a neutral or acid dye bath in deep reddish-brown tones, whereby the dyeing produces excellent light, fulling, chlorine, friction, sweat, seawater, carbonation, water stains -, acid and. Has resistance to alkali stains and heat.
Example: 5 parts by weight of 1- [p- (phenylsulfonyl) - benza.mido] -2-methyl-4- (2-naphthylamino) - anthraquinone (violet powder with a melting point of 249 C after recrystallization from o-dichlorobenzene) were in 23 Parts by weight of 100% sulfuric acid are stirred in and the (2-naphthylamino) anthraquinone is treated with a sulfonating agent in such a way that
that carbazole ring closure occurs and a sulfo group is introduced into the naphthalene nucleus. The reaction mixture was stirred at 40 ° C. for about 4 hours in order to complete the carbazole ring and the sulfonation.
The mixture was then poured into about 250 parts of an ice-cold 40% aqueous sodium sulfate solution, and the precipitate formed was filtered off and washed with a small amount of cold 40% aqueous sodium sulfate solution. The filter cake was suspended in water, neutralized with sodium carbonate and the resulting solution evaporated to dryness, where the carbazole was obtained.
The carbazole obtained is a water-soluble powder in the form of the sodium salt that dyes wool from a neutral or acidic dye bath in deep reddish-brown tones that are slightly yellow and darker than those produced with the dye according to the main patent.
The dyeings obtained with the dye have excellent light, washing, fulling, chlorine, friction, perspiration, sea water, carbonation, water stain, acid and alkali stain and heat fastness.
The dye obtained has the formula
EMI0002.0008
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US310699XA | 1951-06-07 | 1951-06-07 | |
| CH303287T | 1952-05-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310699A true CH310699A (en) | 1955-10-31 |
Family
ID=25734636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310699D CH310699A (en) | 1951-06-07 | 1952-05-02 | Process for the preparation of an anthraquinone naphthocarbazole dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310699A (en) |
-
1952
- 1952-05-02 CH CH310699D patent/CH310699A/en unknown
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