AT158073B - Process for the production of olive-green to green-black sulfur dyes. - Google Patents
Process for the production of olive-green to green-black sulfur dyes.Info
- Publication number
- AT158073B AT158073B AT158073DA AT158073B AT 158073 B AT158073 B AT 158073B AT 158073D A AT158073D A AT 158073DA AT 158073 B AT158073 B AT 158073B
- Authority
- AT
- Austria
- Prior art keywords
- green
- olive
- production
- sulfur dyes
- black
- Prior art date
Links
- 239000000988 sulfur dye Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- -1 cyelohexanol Chemical compound 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung olivgrüner bis grünschwarzer Schwefelfarbstoffe.
Es ist bereits vorgeschlagen worden, mehrkernige Kohlenwasserstoffe oder auch deren Oxy-,
Amino-oder Sulfoderivate in Schwefelfarbstoffe überzuführen, doch ist nach diesem Verfahren kein olivgrüner bis grünsehwarzer Schwefelfarbstoff erhalten worden.
Es wurde nun gefunden, dass sich die nach der deutschen Patentschrift Nr. 627698 erhältlichen
Kondensationsprodukte von Oxy-bzw. Amino-Verbindungen des Pyrens und Chrysens mit Oxyaminobenzolen durch Behandeln mit schwefelnden Mitteln in Sehwefelfarbstoffe überführen lassen, die Baumwolle in olivgrünen bis grünschwarzen Tönen mit guten Echtheitseigenschaften anfärben. Zu ihrer Darstellung werden die genannten Verbindungen nach bekannten, für die Herstellung von Schwefelfarbstoffen üblichen Methoden zweckmässig mit einem Polysulfid bei Gegenwart eines organischen Lösungsmittels, wie Äthylalkohol, Butylalkohol, Cyelohexanol, Pyridin u. dgl., erhitzt.
Es werden aber auch Farbstoffe mit gleichen Eigenschaften erhalten, wenn man die Verschwefelung bei Gegenwart von Benzidin oder einer entsprechenden organisehen Base ausführt.
Beispiel 1 : 40 Teile 4'-Oxyphenyl-2-aminoehrysen werden mit einer aus 24 Teilen wasserfreien Natriumsulfides und 60 Teilen Schwefel in 250 Teilen Butylalkohol dargestellten Polysulfidlösung bis zur Beendigung der Farbstoffbildung gekocht. Nach Verdampfen des Lösungsmittels wird mit einer Kochsalzlösung gewaschen, worauf die Aufarbeitung in üblicher Weise erfolgt. Es werden etwa 62 Teile eines Farbstoffes erhalten, der Baumwolle aus einer Sehwefelnatrium-oder Hydrosulfidküpe in olivgrünen bis grünsehwarzen Tönen mit guter Wasch- und Sodaechtheit anfärbt und auch bereits eine bemerkenswerte Chlorechtheit besitzt.
Beispiel 2 : 40 Teile 4'-Oxyphenyl-3-aminopyren liefern bei der Sehwefelung nach Beispiel l etwa 65 Teile eines in verdünnter Schwefelnatriumlösung dunkelgrün löslichen Farbstoffes, der Baumwolle in olivgrünen bis grünschwarzen Tönen mit den gleichen Eehtheitseigensehaften des Farbstoffes nach Beispiel] anfärbt : er kann gleichfalls auch aus der Hydrosulfitküpe gefärbt werden.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the production of olive-green to green-black sulfur dyes.
It has already been proposed to use polynuclear hydrocarbons or their oxy,
Conversion of amino or sulfoderivatives into sulfur dyes, but no olive-green to green-black sulfur dye has been obtained by this process.
It has now been found that the available according to German Patent No. 627698
Condensation products of oxy or. Amino compounds of pyrene and chrysene with oxyaminobenzenes can be converted into sulfur dyes by treatment with sulphurizing agents, which dye cotton in olive-green to green-black shades with good fastness properties. For their representation, the compounds mentioned are used by known methods customary for the preparation of sulfur dyes, suitably with a polysulfide in the presence of an organic solvent such as ethyl alcohol, butyl alcohol, cyelohexanol, pyridine and the like. Like., heated.
However, dyes with the same properties are also obtained if the sulphurisation is carried out in the presence of benzidine or a corresponding organic base.
Example 1: 40 parts of 4'-oxyphenyl-2-aminoehrysen are boiled with a polysulfide solution prepared from 24 parts of anhydrous sodium sulfide and 60 parts of sulfur in 250 parts of butyl alcohol until the dye has formed. After evaporation of the solvent, it is washed with a sodium chloride solution, whereupon the work-up takes place in the usual way. About 62 parts of a dye are obtained which dyes cotton from a sehulphur sodium or hydrosulfide vat in olive-green to greenish-black shades with good washfastness and soda fastness and also already has remarkable chlorinefastness.
Example 2: 40 parts of 4'-oxyphenyl-3-aminopyrene produce about 65 parts of a dye which is soluble in a dilute sodium sulphide solution and which dyes cotton in olive-green to green-black shades with the same solidity properties of the dye according to Example] when sulfurized according to Example 1: er can also be colored from the hydrosulfite vat.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT158073T | 1938-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT158073B true AT158073B (en) | 1940-03-11 |
Family
ID=3649651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT158073D AT158073B (en) | 1938-05-13 | 1938-05-13 | Process for the production of olive-green to green-black sulfur dyes. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT158073B (en) |
-
1938
- 1938-05-13 AT AT158073D patent/AT158073B/en active
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