CH309807A - Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid. - Google Patents
Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid.Info
- Publication number
- CH309807A CH309807A CH309807DA CH309807A CH 309807 A CH309807 A CH 309807A CH 309807D A CH309807D A CH 309807DA CH 309807 A CH309807 A CH 309807A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- acid
- preparation
- blue
- metal
- Prior art date
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 239000002184 metal Substances 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
- 150000002148 esters Chemical class 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
- 239000002253 acid Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 4
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 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
- 229920000297 Rayon Polymers 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 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
- 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
Zusatzpatent zum Hauptpatent Nr. 306387. verfahren zur Herstellung eines 3'-Oxy-4'-earboxyphenylesters einer metallhaltigen Phthaloeyanintetrasulfonsäure. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines 3'-Oxy- 4' - carboxyphenylesters einer Aluminium- phthalocyanintetrasulfonsäure, welches da durch gekennzeichnet ist, dass man 1 Mol Aluminiumphthalocyanin-3,3',3",
3"'-tetrassulfo- chlorid mit 4 Molen 1,3-Dioxybenzol-4-carbon- säure in Gegenwart einer Mineralsäure neu tralisierenden Substanz zur Umsetzung bringt.
Das zu verwendende Aluminiumphthalo- eyanin-3,3',3",3'-tetrasulfochlorid kann ent weder durch Einwirkung von Chlorsulfon- säure auf Aluminiumphthalocyanin oder durch Einwirkung von Chlorsulfonsäure auf Alumi- niumphthalocyanin-3,3',3",3"'-t.etrasulfonsäure erhalten werden.
Im nachfolgenden Beispiel bedeuten die Teile CTewichtsteile.
Beispiel: 93,3 Teile (1/1o Mol) Aluminiumphthalo- eyanin - 3, 3', 3", 3"' - tetrasulfochlorid werden auf Eis ausgeladen und das abgetrennte Re aktionsprodukt.
als feuchte Paste mit 300 Tei len zerkleinertem Eis vermischt und eine Lö sung von 65 Teilen (4/loMol) 1,3-Dioxybenzol- 4-earbonsäure und 34 Teilen Natriumhydroxyd (100 %) in 300 Teilen Wasser zugegeben. Nach mehrstündigem Rühren bei Raumtemperatur wird der Farbstoff durch Aussalzen mit Koch salz als Natriumsalz isoliert.
Das Natriumsalz des 3'-Oxy-4'-carboxy- phenylesters der Aluminiumphthalocyanin- 3,3',3",3"'-tetrasulfonsäure stellt ein blau- grünes Pulver dar, das sich in Wasser mit blauer und in konz. Schwefelsäure mit grüner Farbe löst.
Der neue Farbstoff eignet sich zum Fär ben von Wolle, Naturseide, Baumwolle und Viskose. Durch Metallsalznachbehandlung wer den die Nassechtheiten zum Teil erheblich ver bessert. Im Chromdruck auf Baumwolle wird ein reines, grünstichiges Blau von sehr guten Echtheiten erhalten.
Additional patent to main patent No. 306387. Process for the production of a 3'-oxy-4'-earboxyphenyl ester of a metal-containing phthaloeyanine tetrasulfonic acid. The present invention relates to a process for the preparation of a 3'-oxy-4 '- carboxyphenyl ester of an aluminum phthalocyanine tetrasulfonic acid, which is characterized in that 1 mol of aluminum phthalocyanine-3,3', 3 ",
3 "'- tetrassulfochloride reacts with 4 moles of 1,3-dioxybenzene-4-carboxylic acid in the presence of a substance that neutralizes mineral acid.
The aluminum phthalocyanine-3,3 ', 3 ", 3'-tetrasulfochloride to be used can either be produced by the action of chlorosulfonic acid on aluminum phthalocyanine or by the action of chlorosulfonic acid on aluminum phthalocyanine-3,3', 3", 3 " '-t.etrasulfonic acid can be obtained.
In the following example, parts C mean parts by weight.
Example: 93.3 parts (1/10 mol) of aluminum phthalo- eyanine - 3, 3 ', 3 ", 3"' - tetrasulfochloride are discharged onto ice and the reaction product separated off.
mixed as a moist paste with 300 parts of crushed ice and a solution of 65 parts (4 / loMol) of 1,3-dioxybenzene-4-carboxylic acid and 34 parts of sodium hydroxide (100%) in 300 parts of water were added. After several hours of stirring at room temperature, the dye is isolated as the sodium salt by salting out with sodium chloride.
The sodium salt of the 3'-oxy-4'-carboxy-phenyl ester of aluminum phthalocyanine-3,3 ', 3 ", 3"' - tetrasulfonic acid is a blue-green powder that turns blue in water and in conc. Dissolves sulfuric acid with a green color.
The new dye is suitable for dyeing wool, natural silk, cotton and viscose. The wet fastness properties are sometimes considerably improved by subsequent treatment with metal salts. Chrome printing on cotton gives a pure, greenish blue with very good fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH309807T | 1952-01-08 | ||
| CH306387T | 1957-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH309807A true CH309807A (en) | 1955-09-15 |
Family
ID=25735150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH309807D CH309807A (en) | 1952-01-08 | 1952-01-08 | Process for the preparation of a 3'-oxy-4'-carboxyphenyl ester of a metal-containing phthalocyanine tetrasulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH309807A (en) |
-
1952
- 1952-01-08 CH CH309807D patent/CH309807A/en unknown
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