CH309801A - Process for the preparation of an ester of a metal-containing phthalocyanine tetrasulfonic acid. - Google Patents
Process for the preparation of an ester of a metal-containing phthalocyanine tetrasulfonic acid.Info
- Publication number
- CH309801A CH309801A CH309801DA CH309801A CH 309801 A CH309801 A CH 309801A CH 309801D A CH309801D A CH 309801DA CH 309801 A CH309801 A CH 309801A
- Authority
- CH
- Switzerland
- Prior art keywords
- blue
- cotton
- acid
- ester
- preparation
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002184 metal Substances 0.000 title description 2
- 229910052751 metal Inorganic materials 0.000 title description 2
- NUSQOFAKCBLANB-UHFFFAOYSA-N phthalocyanine tetrasulfonic acid Chemical compound C12=CC(S(=O)(=O)O)=CC=C2C(N=C2NC(C3=CC=C(C=C32)S(O)(=O)=O)=N2)=NC1=NC([C]1C=CC(=CC1=1)S(O)(=O)=O)=NC=1N=C1[C]3C=CC(S(O)(=O)=O)=CC3=C2N1 NUSQOFAKCBLANB-UHFFFAOYSA-N 0.000 title 1
- 229920000742 Cotton Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 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 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 241000083869 Polyommatus dorylas Species 0.000 claims description 2
- 229920000297 Rayon Polymers 0.000 claims description 2
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960005219 gentisic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B47/26—Amide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 306387. Verfahren zur Herstellung eines Esters einer metallhaltigen Phthaloeyanintetrasulfonsäure. Gegenstand der vorliegenden Erfindung ist. ein Verfahren zur Herstellung eines Esters einer Kupferphthalocyanintetrasulfonsäure, welches dadurch gekennzeichnet ist, da.ss man 1 Mol Kupferphthalocyanin-3,3',3",3"'-tetra- sulfochlorid mit 4 Molen 1,
4-Dioxybenzol-5- earbonsäure in Gegenwart einer Mineralsäure neutralisierenden Substanz zur Umsetzung bringt.
Das zu verwendende Kupferphthalocyanin- 3, 3', 3", 3"' - tetrasulfochlorid kann entweder durch Einwirkung von Chlorsulfonsäure auf Kupferphthalocyanin oder durch Einwirkung von Chlorsulfonsäure auf Kupferphthaloeya- nin-3,3',3",3"'-tetrasulfonsäure erhalten wer den.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile.
<I>Beispiel:</I> 48,5 Teile (1/2o Mol) Kupferphthalocyanin- 3,3',3",3"'-tetrasulfochlorid werden auf Eis ausgeladen, dass abgesogene Reaktionsprodukt mit 200 Teilen zerkleinertem Eis vermischt und unter Rühren eine Lösung von 32,5 Teilen 2o Mal) 1,4-Dioxybenzol - 5 - carbonsäure (Gentisinsäure) und 17 Teilen Natrium hydroxyd (100 /a)
in 250 Teilen Wasser zu gegeben und während 5 Stunden bei 0-5 C und während weiteren 10 Stunden bei 15 bis 20 C gerührt. Der Farbstoff wird aus der erhaltenen klaren Lösung durch Aussalzen mit Natriumchlorid als Natriumsalz isoliert. Er stellt ein blauviolettes Pulver dar, das sieh in Wasser mit leuchtend blauer und in konz. Schwefelsäure mit gelbgrüner Farbe löst. Der Farbstoff eignet sich gut zum Färben von Baumwolle, Viskose und Nylon sowie zum Färben von vorehromierter Baumwolle und ehromierter Wolle.
Es werden blaugrüne Farbtöne von :sehr guten Nassechtheiten und vorzüglicher Lichtechtheit erhalten. Im Chrom druck auf Baumwolle liefert er türkisblaue Farbtöne von ausgezeichneten Echtheits eigenschaften.
<B> Additional patent </B> to main patent no. 306387. Process for the production of an ester of a metal-containing phthaloeyanine tetrasulfonic acid. The subject of the present invention is. a process for the preparation of an ester of a copper phthalocyanine tetrasulfonic acid, which is characterized in that 1 mole of copper phthalocyanine 3,3 ', 3 ", 3"' - tetrasulfochloride with 4 moles of 1,
Brings 4-dioxybenzene-5-carboxylic acid in the presence of a mineral acid neutralizing substance to the reaction.
The copper phthalocyanine-3, 3 ', 3 ", 3"' -tetrasulfochloride to be used can be obtained either by the action of chlorosulfonic acid on copper phthalocyanine or by the action of chlorosulfonic acid on copper phthaloeyanine-3,3 ', 3 ", 3"' - tetrasulfonic acid will.
In the following example, the parts are parts by weight.
<I> Example: </I> 48.5 parts (1 / 2o mol) of copper phthalocyanine 3,3 ', 3 ", 3"' - tetrasulfochloride are unloaded onto ice, the suctioned reaction product mixed with 200 parts of crushed ice and under Stir a solution of 32.5 parts 2o times) 1,4-dioxybenzene - 5 - carboxylic acid (gentisic acid) and 17 parts sodium hydroxide (100 / a)
added in 250 parts of water and stirred for 5 hours at 0-5 C and for a further 10 hours at 15-20 C. The dye is isolated as the sodium salt from the clear solution obtained by salting out with sodium chloride. It is a blue-violet powder that looks bright blue in water and in conc. Sulfuric acid dissolves with a yellow-green color. The dye is well suited for dyeing cotton, viscose and nylon as well as for dyeing pre-chromed cotton and honed wool.
Blue-green shades of: very good wet fastness and excellent light fastness are obtained. With chrome printing on cotton, it delivers turquoise blue shades with excellent fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH309801T | 1952-01-08 | ||
| CH306387T | 1957-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH309801A true CH309801A (en) | 1955-09-15 |
Family
ID=25735144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH309801D CH309801A (en) | 1952-01-08 | 1952-01-08 | Process for the preparation of an ester of a metal-containing phthalocyanine tetrasulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH309801A (en) |
-
1952
- 1952-01-08 CH CH309801D patent/CH309801A/en unknown
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