DEP0000837DA - Process for the production of sulfur dyes. - Google Patents
Process for the production of sulfur dyes.Info
- Publication number
- DEP0000837DA DEP0000837DA DEP0000837DA DE P0000837D A DEP0000837D A DE P0000837DA DE P0000837D A DEP0000837D A DE P0000837DA
- Authority
- DE
- Germany
- Prior art keywords
- production
- sulfur dyes
- dyes
- dinitrophenyl
- brown
- 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.)
- Expired
Links
- 239000000988 sulfur dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 3
- -1 dinitrophenyl Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Description
J.M.DANNER RefoNo.l906JMDANNER Ref o No.l906
Dr0W.ZERWECKDr 0 W.ZERWECK
Dr.Bu/Sto Frankfurt a/M=Feehenheim den 31„August 194SDr.Bu / Sto Frankfurt a / M = Feehenheim on August 31, 194S
Verfahren zur Herstellung vos Sehwefelfarbstof fen„Process for the production of sulfur dyes "
Es wurde gefunden, dass man zu wertvollen Sehwefelfarb^ stoffen gelangt, wenn man Verblödungen, in denen zwei Diaitrophenyl=* gruppen mittels Aminogruppen durch Polymethiak@tten? welche gegeb®»= nenfalle durch andere Atome oder Atomgruppen unterbrochen sein könne« verbunden sind, in an sieh bekannter Weise mit schwefelnden Mitteln behandelt«It has been found that valuable sulfur dyes can be obtained if one kills two diaitrophenyl groups by means of amino groups through polymethiac @ ? which "= traps could be interrupted by other atoms or atomic groups" are connected, treated in a known manner with sulphurous agents "
Diese Verbindungen lassen sich z„B„ durch Kondensation von 2.4*~Diaitro-halQgenbenzol mit einem entsprechenden Pplymethylendi&mi» herstellen.These compounds can be obtained, for example, by condensing 2.4% diaitro-halobenzene with a corresponding polymethylene di & mi » produce.
Die so erhaltenen Farbstoffe färben die pflanzliche Faser aus de» Sehwefeln&triumbade iu wertvollen braunen Farbtönen von gute»»The dyes obtained in this way color the vegetable fibers from the »Sehwefeln & triumbade iu valuable brown shades of good» »
Beispiel ,1 tExample, 1 t
610 g/Sehwefelnatrius ^rist. und £10 g/'Schwefel werden bei etwa 105-110o>'^usammefagasehmolzen* In das so gebildete Polysulfid werden bei 110=120° in kleines Anteilen 250 gT Di-(2e4-<lin.itr©pfc@uyl!~ äthyleadiamin (beschrieben in Jepr.Ch.48/202) eingetragen? die R@ak® tioasaasse wird schließlich zur Trockne eingedampft. D^nn wird auf 260° geheizt und 8 Stunden bei dieser Temperatur gehalten« Nach dem Erkaltes wird die erhalten© Rohsehm«lze gemahlen.610 g / Sehwefelnatrius ^ rist. and £ 10 g / 'sulfur at about 105-110 o>' * In the thus formed polysulfide at 110 = 120 ° ^ usammefagasehmolzen in small portions 250 gT di- (2 s 4- <lin.itr©pfc@uyl ! ~ ethyleadiamine (described in J e pr.Ch.48 / 202) entered? the R @ ak® tioasasse is finally evaporated to dryness. D ^ nn is heated to 260 ° and kept at this temperature for 8 hours they are grounded raw clay.
Der auf diese Weise erhaltene Farbstoff färbt Baumwolle ±» kräftigen dunkelbraunen Tönen von guten Echtheitseigeasehaften«The dye obtained in this way dyes cotton ± "strong dark brown tones with good fastness properties"
Baispiel 2 ;Example 2;
200 s/ Di-(2.4-dinitrophenyl)-athyleadiamin und 40 g^ Kupfersulfat werden bei etwa 120° in Polysulfide das aus 600 g/" Schwefel® natrium krist. und 36s? g^ Schwefel gebildet ist§ langsam eingetragen bis die Reaktion beendet ist* Dann wird die Schmelze zur Iroek»e ein200 s / di- (2,4-dinitrophenyl) -athyleadiamin and 40 g ^ copper sulfate at about 120 ° in the polysulfides is formed from 600 g / "Schwefel® sodium cryst. And 36 s? G ^ § sulfur added slowly to the reaction is finished * Then the melt becomes an Iroek »e one
gedampft^ auf 260° erhitzt'und bei dieser Temperatur 8 Stunden gehalten« D@i» so erhaltene Farbstoff färbt Baumwolle in stärkere» TO«steamed ^ heated to 260 ° and held at this temperature for 8 hours "D @ i" the dye obtained dyes cotton in stronger "TO"
neu als der des Beispiels 1 und zeigt im übrigen die gleiche Muane® Echtheit οnew than that of example 1 and otherwise shows the same Muane® authenticity ο
Nachstehend folgt eine Uebersicht der Nuancen von anderen Farbstoffen, die nach dem Verfahren vorliegender Erfindung erhalten werden.The following is an overview of the nuances of other dyes obtained by the process of the present invention will.
AusgangSTnaterialOutput ST material
des Nuance doPärbg Ausgangs=- auf Baumwolle
materialsdes nuance d o color output = - on cotton
materials
Di~(2,,4-dinitrophenyl)<=tetramethyl@ndiamin 232( Di ~ (2,, 4-dinitrophenyl) <= tetramethyl @ ndiamin 232 (
Di-(2 ο 4-dinitrophenyl)-hexamethylendiamin Di-(2„4-dinitrophenyl)-piperaz in ■y·. V-Di-(2.4-dinitrophenyl amino) 0 dipropylätherDi- (2 o 4-dinitrophenyl) -hexamethylenediamine di- (2 "4-dinitrophenyl) -piperaz in ■ y ·. V-di- (2.4-dinitrophenyl amino) 0 dipropyl ether
β„β *-Di=C 2 ο 4-dinitrophenylamino) =β "β * -Di = C 2 ο 4-dinitrophenylamino) =
diäthylamindiethylamine
Kondensationsprodukt aus äqu!molekularen Mengen von 1.5-Diehlor-2o4-dinitrobenzol und AethylendiaminCondensation product from equivalent molecular amounts of 1,5-diehlor-2 o 4-dinitrobenzene and ethylenediamine
202'202 '
gelbbraun
rotstieh,, braunyellow-brown
rotstieh ,, brown
zerso240° bronze
157/158° gelbstichcöraunzerso240 ° bronze
157/158 ° yellowish corrugated brown
über 300° kastanienbraunover 300 ° chestnut brown
Claims (1)
Family
ID=
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