AT39139B - Process for the preparation of monobromo trichloroindigo. - Google Patents
Process for the preparation of monobromo trichloroindigo.Info
- Publication number
- AT39139B AT39139B AT39139DA AT39139B AT 39139 B AT39139 B AT 39139B AT 39139D A AT39139D A AT 39139DA AT 39139 B AT39139 B AT 39139B
- Authority
- AT
- Austria
- Prior art keywords
- trichloroindigo
- preparation
- monobromo
- indigo
- additional patent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 7
- 229940097275 indigo Drugs 0.000 description 7
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 7
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZLHGTHCCYUEAIK-UHFFFAOYSA-N 5,7-dibromo-2-(5,7-dibromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2c(Br)cc(Br)cc12)C1=[NH+]c2c(cc(Br)cc2Br)C1=O ZLHGTHCCYUEAIK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Monobromtrichlorindigo.
Im Patente Nr. 32207 ist die Herstellung von Tri-und Tetrabromderivaten des Indigos beschrieben. Es wurde nun gefunden, dass man zu einem neuen wertvollen Tetrahalogenderivat des Indigos gelangen kann, indem man den durch Chlorieren von Indigo
EMI1.1
indigo in der Wärme und unter Benutzung indifferenter Verdünnungsmittel der Bromierung unterwirft. Der hierbei entstehende Monobromtrichlorindigo liefert beim Färben aus alkalischer Kupe reine blaue Nuancen, welche erheblich rotstichiger sind, als die mittelst Tetrabromindigo (Patent 32207) erzeugten Töne. Die Färbungen besitzen bei guter Waschund Chlorechtheit ausserdem eine ganz vorzügliche Lichtechtheit, weiche diejenige der bekannten Polyhalogenderivato des Indigos bedeutend übertrifft und selbst den höchsten Anforderungen genügen dürfte.
B e i s p i e l.
10 Teile Trichiorindigo (dargestellt durch Chlorieren von Indigo in Nitrobenzol bei
EMI1.2
badtemperatur) erhitzt. Nach weiterem 1-2 stündigem Erhitzen bei dieser Temperatur lässt man erkalten, filtriert den ausgeschiedenen Farbstob ab, wäscht mit Alkohol und trocknet. Der so erhaltene Monohromtrichlorindigo bildet kupferglänzende, violettbraune Kriställchen, die sich in konzentrierter Schwefelsäure mit rein blauer, in rauchender Schwefelsaure mit grüstichig blauer Farbe lösen. In Anilin ist er in der Kälte kaum. zlemlir leicht dagegen in der Wärme mit rein blauer Farbe löslich. Seine Lösung in Itrobenzol ist blauviolett gefärbt.
Baumwolle wird aus alkalischer Küpe in reinen blauen Tonen anwarbt, die sich wie bereits erwähnt, ausser durch gute Wasch- und Chlor- echthot durch eino vorzügliche Lichtechtheit auszeichnen.
In orsthondom Beispiel kann das Nitrobenzol auch durch andere indifferente Verdünnungs- bezw. Lösungsmittel ersetzt werden. Ferner kann man die Bromierung auch unter Zusatz von Halogenüberträgern vornehmen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of monobromo trichloroindigo.
The production of tri- and tetrabromo derivatives of indigo is described in patent no. 32207. It has now been found that a new valuable tetrahalogen derivative of indigo can be obtained by chlorinating indigo
EMI1.1
Indigo subjected to bromination in the warmth and with the use of indifferent diluents. The resulting monobromo trichloroindigo provides pure blue nuances when dyeing from alkaline copper which are considerably more reddish than the tones produced by means of tetrabromoindigo (patent 32207). In addition to being good fastness to washing and chlorine, the dyeings also have very excellent lightfastness, which significantly exceeds that of the known polyhalogen derivatives of indigo and should even meet the highest requirements.
Ex ample.
10 parts of trichiorindigo (made by chlorinating indigo in nitrobenzene at
EMI1.2
bath temperature). After heating for a further 1-2 hours at this temperature, the mixture is left to cool, the precipitated dye is filtered off, washed with alcohol and dried. The monochlorine indigo obtained in this way forms copper-shining, violet-brown crystals which dissolve in concentrated sulfuric acid with a pure blue color, in fuming sulfuric acid with a shabby blue color. In aniline he is hardly in the cold. On the other hand, they are easily soluble in heat with a pure blue color. Its solution in itrobenzene is blue-violet in color.
Cotton is advertised from an alkaline vat in pure blue tones, which, as already mentioned, are characterized by excellent lightfastness, in addition to being good for washing and chlorine.
In orsthondom example, the nitrobenzene can also be used by other indifferent diluents. Solvent to be replaced. Furthermore, the bromination can also be carried out with the addition of halogen carriers.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT32207T | 1907-03-04 | ||
| AT39139T | 1908-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT39139B true AT39139B (en) | 1909-10-11 |
Family
ID=25599735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT39139D AT39139B (en) | 1907-03-04 | 1908-08-23 | Process for the preparation of monobromo trichloroindigo. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT39139B (en) |
-
1908
- 1908-08-23 AT AT39139D patent/AT39139B/en active
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