CH367918A - Process for the production of sulfur dyes of the phthalocyanine series - Google Patents
Process for the production of sulfur dyes of the phthalocyanine seriesInfo
- Publication number
- CH367918A CH367918A CH5928458A CH5928458A CH367918A CH 367918 A CH367918 A CH 367918A CH 5928458 A CH5928458 A CH 5928458A CH 5928458 A CH5928458 A CH 5928458A CH 367918 A CH367918 A CH 367918A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- sulfur dyes
- metal
- parts
- phthalocyanine series
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000988 sulfur dye Substances 0.000 title claims description 4
- -1 metal complex salts Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- NGDNCZPCIZNCQS-UHFFFAOYSA-N ctk3j8699 Chemical compound Cl=S NGDNCZPCIZNCQS-UHFFFAOYSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 7
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 3
- 229940010552 ammonium molybdate Drugs 0.000 description 3
- 235000018660 ammonium molybdate Nutrition 0.000 description 3
- 239000011609 ammonium molybdate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 2
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- C09B49/00—Sulfur dyes
- C09B49/12—Sulfur dyes from other compounds, e.g. other heterocyclic compounds
- C09B49/122—Sulfur dyes from other compounds, e.g. other heterocyclic compounds from phthalocyanine compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von Schwefelfarbstoffen der Phthalocyaninreihe Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung von Schwefelfarbstoffen der Phthalo- cyaninreihe, dadurch gekennzeichnet,
dass man auf metallfreie Polyanünophthalocyanine oder deren Metallkomplexsalze Chlorsulfonsäure und mindestens 5 Mol Chlorschwefel pro Mol der Polyaminophthalo- cyaninverbindung bei einer Temperatur von 70 bis 150 einwirken lässt. Die so erhaltenen Farbstoffe be sitzen grünstichig bis blaustichig olivgraue Farbnuan cen und sie liefern Färbungen von ausgezeichneter Lichtechtheit.
Es wurde nunmehr gefunden, dass man dieses Verfahren vorteilhaft derart ausführen kann, dass man auf ein durch Einwirkung von Hydroxylamin oder Hydroxylamin liefernden Substanzen in Chlorsulfon- säure auf metallfreie Phthalocyanine oder deren Metallkomplexsalze in Gegenwart von Verbindungen von Elementen der 5. oder 6. Gruppe des peri odischen 'Systems (wie z.
B. Ammoniummolybdat oder Vanadiumpentoxyd) erhaltenes, metallfreie Poly- aminophthalocyamine oder Metallkomplexsalze der selben enthaltendes Reaktionsgemisch mindestens 5 Mol Chlorschwefel pro Mol der Phthalocyaninverbin- dung bei einer Temperatur von 70 bis 150 C ein wirken lässt.
<I>Beispiel 1</I> 23 Teile Kupferphthalocyanin, 15,6 Teile 95o/oiges Hydroxylaminsulfat und 0,11 Teile Am- moniummolybdat werden in 345 Teilen Chlorsulfon- säure 2 Stunden bei 115 gerührt. Dann werden in nerhalb 10-15 Minuten 40,5 Teile Chlorschwefel eingetropft. Dieses Gemisch wird 1 Stunde bei 115 gerührt und nach Abkühlen auf 30 in die 5-6-fache Menge Wasser gegossen.
Der in bekannter Weise isolierte Farbstoff färbt die Textilfaser aus stumpf stahlblauer Schwefelnatriumlösung in grünstichig oliv- grauen Tönen von guter Wasch- und sehr guter Licht echtheit.
Rührt man mit Hydroxylamin nicht 2 Stunden bei 115 sondern 3 Stunden bei 105 unter sonst unveränderten Versuchsbedingungen, so erhält man einen -etwas blaustichigeren Farbstoff von gleichen Echtheitseigenschaften.
Rührt man mit Chlorschwefel nicht 1 sondern 3 Stunden und arbeitet sonst unter den gleichen Be dingungen, so erhält man einen Farbstoff von prak tisch den gleichen Eigenschaften.
<I>Beispiel 2</I> 23 Teile Kupferphthalocyanin, 15,6 Teile 95 1/oiges Hydroxylaminsulfat und 0,11 Teile Am- moniummolybdat werden in 345 Teilen Chlorsulfon- säure 24 Stunden bei 85 gerührt.
Dann werden in nerhalb 10-15 Minuten 40,5 Teile Chlorschwefel eingetropft. Dieses Gemisch wird 2 Stunden bei 85 gerührt und nach Abkühlen auf etwa 30 in die 5-6fache Menge Wasser eingetropft. Der in üblicher Weise isolierte Farbstoff färbt die Textilfaser aus schmutzig blaugrüner Schwefelnatriumlösung in blau stichig olivgrauen Tönen von guter Wasch- und sehr guter Lichtechtheit.
Ersetzt man die in diesem Beispiel verwendeten 15;6 Teile 95 o/o@iges Hydroxylaminsulfat durch 25,9 Teile 91 o/oiges saures Hydroxylaminsulfat (NH20H # H2SO4), so erhält man ein Produkt mit praktisch gleichen fär- berischen Eigenschaften.
Process for the production of sulfur dyes of the phthalocyanine series The subject of the main patent is a process for the production of sulfur dyes of the phthalocyanine series, characterized in that
that chlorosulfonic acid and at least 5 moles of chlorosulfur per mole of the polyaminophthalocyanine compound are allowed to act at a temperature of 70 to 150 on metal-free polyamino phthalocyanines or their metal complex salts. The dyes obtained in this way have greenish to bluish olive-gray shades and they give dyeings of excellent lightfastness.
It has now been found that this process can advantageously be carried out in such a way that one reacts to a substance in chlorosulfonic acid which is provided by the action of hydroxylamine or hydroxylamine on metal-free phthalocyanines or their metal complex salts in the presence of compounds of elements of the 5th or 6th group of the periodic 'system (such as
B. ammonium molybdate or vanadium pentoxide) obtained, metal-free polyaminophthalocyamines or metal complex salts of the same containing reaction mixture at least 5 moles of chlorosulfur per mole of the phthalocyanine compound at a temperature of 70 to 150 ° C can act.
<I> Example 1 </I> 23 parts of copper phthalocyanine, 15.6 parts of 95% hydroxylamine sulfate and 0.11 part of ammonium molybdate are stirred in 345 parts of chlorosulfonic acid at 115 for 2 hours. Then 40.5 parts of sulfur chloride are added dropwise within 10-15 minutes. This mixture is stirred for 1 hour at 115 and, after cooling to 30, poured into 5-6 times the amount of water.
The dye, which is isolated in a known manner, dyes the textile fiber from a dull steel-blue sodium sulphide solution in greenish olive-gray shades of good fastness to washing and very good lightfastness.
If the mixture is stirred with hydroxylamine not at 115 for 2 hours but at 105 for 3 hours under otherwise unchanged test conditions, a dye with a somewhat bluish cast and the same fastness properties is obtained.
If you stir with chlorosulfur for 3 hours rather than 1 and otherwise work under the same conditions, you get a dye with practically the same properties.
<I> Example 2 </I> 23 parts of copper phthalocyanine, 15.6 parts of 95% hydroxylamine sulfate and 0.11 part of ammonium molybdate are stirred in 345 parts of chlorosulfonic acid at 85 for 24 hours.
Then 40.5 parts of sulfur chloride are added dropwise within 10-15 minutes. This mixture is stirred for 2 hours at 85 and, after cooling to about 30, is added dropwise to 5-6 times the amount of water. The dye, isolated in the usual way, dyes the textile fiber from dirty blue-green sodium sulphide solution in blue-tinged olive-gray shades of good washing fastness and very good lightfastness.
If the 15.6 parts of 95% hydroxylamine sulphate used in this example are replaced by 25.9 parts of 91% acidic hydroxylamine sulphate (NH20H.H2SO4), a product is obtained with practically the same coloring properties.
Claims (1)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US629239A US2832789A (en) | 1953-07-02 | 1956-12-19 | Sulfur dyestuffs of the phthalocyanine series |
| DEC14808A DE1062852B (en) | 1957-05-10 | 1957-05-10 | Process for the production of gray sulfur dyes of the phthalocyanine series |
| DE1957C0014807 DE1067154B (en) | 1957-05-10 | 1957-05-10 | PROCESS FOR THE PREPARATION OF GRAY SULFUR DYES OF THE PHTALOCYANINE SERIES |
| DEC15077A DE1058663B (en) | 1956-12-19 | 1957-06-27 | Process for the production of sulfur dyes of the phthaloxyanine series |
| DEC15078A DE1062369B (en) | 1956-12-19 | 1957-06-27 | Process for the production of sulfur dyes of the phthalocyanine series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH367918A true CH367918A (en) | 1963-03-15 |
Family
ID=27511952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5928458A CH367918A (en) | 1956-12-19 | 1958-05-08 | Process for the production of sulfur dyes of the phthalocyanine series |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH367918A (en) |
-
1958
- 1958-05-08 CH CH5928458A patent/CH367918A/en unknown
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