DE215747C - - Google Patents
Info
- Publication number
- DE215747C DE215747C DENDAT215747D DE215747DA DE215747C DE 215747 C DE215747 C DE 215747C DE NDAT215747 D DENDAT215747 D DE NDAT215747D DE 215747D A DE215747D A DE 215747DA DE 215747 C DE215747 C DE 215747C
- Authority
- DE
- Germany
- Prior art keywords
- trichloroindigo
- indigo
- nitrobenzene
- warmth
- bromine
- 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.)
- Active
Links
- 229940097275 Indigo Drugs 0.000 claims description 5
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 240000007871 Indigofera tinctoria Species 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 241001062009 Indigofera Species 0.000 description 4
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PTWYQANXSNMUTI-YPKPFQOOSA-N (2Z)-5,7-dibromo-2-(5,7-dibromo-3-oxo-1H-indol-2-ylidene)-1H-indol-3-one Chemical compound N1C=2C(Br)=CC(Br)=CC=2C(=O)\C1=C(C1=O)\NC2=C1C=C(Br)C=C2Br PTWYQANXSNMUTI-YPKPFQOOSA-N 0.000 description 1
- KUGFODPTKMDJNG-UHFFFAOYSA-I Antimony pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[SbH3+3] KUGFODPTKMDJNG-UHFFFAOYSA-I 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010992 reflux Methods 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
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
- C09B7/00—Indigoid dyes
- C09B7/02—Bis-indole indigos
- C09B7/04—Halogenation thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-Ja 215747■-KLASSE 22 e. GRUPPE -Yes 215747 ■ CLASS 22 e. GROUP
in BASEL.in Basel.
Zusatz zum Patente 193438 vom 27. Januar 1907.*)Addendum to patent 193438 of January 27, 1907. *)
Patentiert im Deutschen Reiche vom 23.August 1908 ab. Längste Dauer: 26. Januar 1922.Patented in the German Empire on August 23, 1908. Longest duration: January 26, 1922.
Es wurde gefunden, daß man zu einem neuen wertvollen Tetrahalogenderivat des Indigos gelangen kann, wenn man den durch Chlorieren von Indigo z. B. gemäß Verfahren der amerikanischen Patentschrift 899863 erhältlichen Trichlorindigo. in der Wärme und unter Benutzung indifferenter Verdünnungsmittel bromiert. Der hierbei entstehende Monobromtrichlorindigo liefert beim Färben aus alkalischer Küpe reine blaue Nuancen, welche erheblich rotstichiger sind als die mittels Tetrabromindigo (Patent 193438) erzeugten Töne. Die Färbungen besitzen bei guter Wasch- und Chlorechtheit außerdem eine ganz vorzügliche Lichtechtheit, welche diejenige der bekannten Polyhalogenderivate des Indigos bedeutend übertrifft und selbst den höchsten Anforderungen genügen dürfte.It has been found that a new valuable tetrahalogen derivative of indigo can be obtained can get if one z by chlorinating indigo. B. according to the method of American patent 899863 available Trichloroindigo. in the warmth and with the use of indifferent diluents brominated. The resulting monobromo trichloroindigo provides pure blue nuances when dyeing from an alkaline vat, which are considerably more reddish than those produced by means of tetrabromoindigo (patent 193438) Sounds. The dyeings also have a very good fastness to washing and chlorine excellent lightfastness, which is that of the known polyhalogen derivatives of indigo significantly exceeds and should even meet the highest requirements.
10 Teile Trichlorindigo (dargestellt z. B. durch Chlorieren von Indigo in Nitrobenzol bei Gegenwart von Antimonpentachlorid gemäß der amerikanischen Patentschrift 899863) werden in 100 bis 120 Teilen Nitrobenzol suspendiert, 6 Teile Brom hinzugefügt und die Mischung im Ölbad am Rückflußkühler im Verlauf von ix/2 Stunden auf 220 bis 2250 (Ölbadtemperatur) erhitzt. Nach weiterem ι bis 2 stündigem Erhitzen bei dieser Temperatur läßt man erkalten, filtriert den ausgeschiedenen Farbstoff ab, wäscht mit Alkohol 35 10 parts of trichloroindigo (prepared, for example, by chlorinating indigo in nitrobenzene in the presence of antimony pentachloride according to American patent 899863) are suspended in 100 to 120 parts of nitrobenzene, 6 parts of bromine are added and the mixture is mixed in an oil bath on a reflux condenser over a period of i x / 2 hours heated to 220 to 225 0 (oil bath temperature). After further 2 hours of heating to ι at this temperature is allowed to cool, filtered from the precipitated dye, washed with alcohol 35
der Wärme mit Seine Lösung in Baumund trocknet. Der so erhaltene Monobromtrichlorindigo
bildet kupferglänzende, violettbraune Kristallenen, die sich in konzentrierter
Schwefelsäure mit rein blauer, in rauchender Schwefelsäure mit grünstichig blauer Farbe
lösen. In Anilin ist er in der Kälte kaum, ziemlich leicht dagegen in
rein bläuer Farbe löslich.
Nitrobenzol ist blauviolett gefärbt,
wolle wird aus alkalischer Küpe in reinen blauen Tönen angefärbt, die sich, wie bereits
erwähnt, außer durch gute Wasch- und Chlorechtheit durch eine vorzügliche Lichtechtheit
auszeichnen.the heat with its solution in tree and dry. The monobromo trichloroindigo obtained in this way forms shiny copper, violet-brown crystals, which dissolve in concentrated sulfuric acid with a purely blue color, in fuming sulfuric acid with a greenish blue color. In aniline it is seldom in the cold, but quite light in
pure blue color soluble.
Nitrobenzene is colored blue-violet,
Wool is dyed from an alkaline vat in pure blue tones, which, as already mentioned, are not only characterized by good fastness to washing and chlorine but also excellent lightfastness.
In vorstehendem Beispiel kann das Nitrobenzol auch durch andere indifferente Verdünnungs- bzw. Lösungsmittel ersetzt werden. Ferner kann man die Bromierung auch unter Zusatz von Halogenüberträgern vornehmen.In the above example, the nitrobenzene can also be replaced by other inert diluents or solvents are replaced. The bromination can also be carried out with the addition of halogen carriers.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE215747C true DE215747C (en) |
Family
ID=477216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT215747D Active DE215747C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE215747C (en) |
-
0
- DE DENDAT215747D patent/DE215747C/de active Active
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