AT43879B - Process for the preparation of sulfur-containing dyes of the anthracene series - Google Patents
Process for the preparation of sulfur-containing dyes of the anthracene seriesInfo
- Publication number
- AT43879B AT43879B AT43879DA AT43879B AT 43879 B AT43879 B AT 43879B AT 43879D A AT43879D A AT 43879DA AT 43879 B AT43879 B AT 43879B
- Authority
- AT
- Austria
- Prior art keywords
- sulfur
- preparation
- containing dyes
- anthracene series
- pyridine
- Prior art date
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims 3
- 229910052717 sulfur Inorganic materials 0.000 title claims 3
- 239000011593 sulfur Substances 0.000 title claims 3
- 150000001454 anthracenes Chemical class 0.000 title claims 2
- 238000000034 method Methods 0.000 title claims 2
- 239000000975 dye Substances 0.000 title 1
- 239000003513 alkali Substances 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 229920001021 polysulfide Polymers 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- AWACQBFBMROGQC-UHFFFAOYSA-N 1-amino-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2N AWACQBFBMROGQC-UHFFFAOYSA-N 0.000 description 1
- FLEURRNKVDUGOR-UHFFFAOYSA-N 1-chloro-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] FLEURRNKVDUGOR-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
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EMI1.4
<Desc/Clms Page number 2>
EMI2.1
Aus Pyridin erhält man gelbliche Krystalle, deren Lösung in konzentrierter Schwefelsäure rot, in Alkali violett rot ist.
Beispiel 3.
EMI2.2
daraus gewonnene Merkaptan krystallisiert aus Pyridin in dunkelblauen Nadeln, deren Lösung in Pyridin violett, in konzentrierter Schwefelsäure anfangs schmutzigbraun, dann violett ist.
Durch Sulfieren erhält man einen violetten Wollfarbstofl.
Beispiel 4.
10 kg 1-Chlor-4-aminoanthrachinon (erhalten durch Reduktion des 1-Chlor-4-nitroanthrachinons) werden mit 150 kg Alkohol und 150 kg einer 28%igen natriumsulfhydratlösung 10 Stunden am Rückflusskühler gekocht. Beim Erkalten scheidet sich das Natronsalz des 4-Aminoanthrachinon-1-merkaptans krystallinisch ab und wird wie bekannt isoliert. In Wasser löst es sich mit blauer Farbe. Mit verdünnter Säure zerlegt und aus Pyridin umkrystallisiert, bildet es bronzeglänzende Nadeln, die sich in Pyridin violettrot, in konzentrierter Schwefelsäure orangegelb lösen.
<Desc / Clms Page number 1>
EMI1.1
EMI1.2
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EMI2.1
Yellowish crystals are obtained from pyridine, the solution of which is red in concentrated sulfuric acid and purple-red in alkali.
Example 3.
EMI2.2
Mercaptan obtained from it crystallizes from pyridine in dark blue needles, the solution of which in pyridine is violet, in concentrated sulfuric acid initially dirty brown, then violet.
Sulfation gives a purple wool dye.
Example 4.
10 kg of 1-chloro-4-aminoanthraquinone (obtained by reducing 1-chloro-4-nitroanthraquinone) are refluxed for 10 hours with 150 kg of alcohol and 150 kg of a 28% strength sodium sulfhydrate solution. On cooling, the sodium salt of 4-aminoanthraquinone-1-mercaptan separates out crystalline and is isolated as is known. It dissolves in water with a blue color. Disassembled with dilute acid and recrystallized from pyridine, it forms shiny bronze needles that dissolve violet-red in pyridine and orange-yellow in concentrated sulfuric acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1908206536D DE206536C (en) | 1908-01-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT43879B true AT43879B (en) | 1910-09-10 |
Family
ID=5793005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT43879D AT43879B (en) | 1908-01-28 | 1909-02-11 | Process for the preparation of sulfur-containing dyes of the anthracene series |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT43879B (en) |
-
1909
- 1909-02-11 AT AT43879D patent/AT43879B/en active
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