CH249635A - Process for the production of a new phthalocyanine derivative. - Google Patents
Process for the production of a new phthalocyanine derivative.Info
- Publication number
- CH249635A CH249635A CH249635DA CH249635A CH 249635 A CH249635 A CH 249635A CH 249635D A CH249635D A CH 249635DA CH 249635 A CH249635 A CH 249635A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- phthalocyanine
- copper
- new
- phthalocyanine derivative
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 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 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- -1 m-nitrobenzene-sulfonylamino Chemical group 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000012265 solid product Substances 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 239000001007 phthalocyanine dye Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical class OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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
- C09B56/00—Azo dyes containing other chromophoric systems
- C09B56/14—Phthalocyanine-azo dyes
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
-
- 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
- C09B47/22—Obtaining compounds having nitrogen atoms directly bound to the phthalocyanine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Imperial Chemical Industries Limited, London (Grossbritannien). Verfahren zur Herstellung eines neuen Phthaloeyaninderivates. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines neuen Phthalocyaninfarb,stoff - Zwischenproduktes, welches dadurch gekennzeichnet ist, dass Kup fer - tetra - 4 -(in - nitrobenzol -,sulfonylamino)
- phthalocyanin zum Kupfer-tetra-4-(m-arnino- henzol-sulfonylamino)-phthalocyanin. redu ziert wird.
Die Reduktion lässt sich in der für die Re duktion von Nitroverbindungen zu Aminover- bindungen bekannten Weise, beispielsweise durch Einwirkung von Alkalimetallsulfiden, Schwefelwasserstoffen, Polysulfiden, Sulfi- ten, Bis.ulfiten oder Hydrosulfiten, oder mit Hilfe von Zinn, Zink, oder Stannochlorid und Säure durchführen.
Das erfindungsgemäss anfallende neue Phthalocyaninzwischenprodukt ist ein dunk les, bläulichgrünes, festes Produkt, welches in Wasser unlöslich ist, jedoch unter Bildung einer Diazoniumverbindung, welche zur Her stellung von Azofarbstoffen Verwendung fin den kann, diazotiert werden kann.
Beispiel: Die i(1%ige Paste von Kupfer-tetra-4- (m-nitrobenzol-sulfonylamino)-pht3ialocyanin (erhalten in der weiter unten beschriebenen Weise) wird bei 0, bis 5 C gerührt und mit 147 Teilen konz. Salzsäure vom spez. Gew. 1,18 versetzt.
Dann wird eine Lösung von 160 Teilen Stannochlorid-Dihydrat in 200 Teilen Wasser hinzugegeben und das Gemisch wäh- rend 16 Stunden gerührt, wobei man die Tem peratur langsam auf 20 C ansteigen lässt. Das Produktwirdfiltriertunddaszurückbleibende feste Produkt so lange gründlich mit ver dünnter Salzsäure gewaschen, bis es keine Zinnsalze mehr enthält, worauf es mit Was ser und schliesslich mit verdünnter Ammo- niumhydrogydlösung gewaschen wird.
An- , schliessend wird noch so lange gewaschen, bis der Rückstand ammoniakfrei ist. Das so er haltene Kupfer-tetra-4-(m-aminobenzol-sul- fonylamino)-phthalocyanin kann zu einem dunkelbläulichgrünen Produkt getrocknet. werden, doch wird man es zu Gebrauchs zwecken vortelhafterweise in Form einer wässrigen Paste aufbewahren.
Die wässrige Paste des in diesem Beispiel verwendeten Kupfer-tetra-4-(m-nitrobenzol- sulfonylamino)-phthalocyanins wird wie folgt hergestellt: Eine wässrige, <B>10,5</B> Teile Kupfer-tetra-4- aminophthalocyanin enthaltende Paste wird filtriert und der Filterkuchen mit Aceton ge waschen, bis er wasserfrei ist.
Hierauf wird der acetonfeuchte Filterkuchen in<B>178</B> Teile trockenes Nitrobenzol eingetragen und die Temperatur des so erhaltenen Gemisches der massen erhöht, bis das Aceton abdestilliert ist. Dann versetzt man diese Suspension mit 50 Teilen m-Nitrobenzol-sulfonylchlorid und lässt die Temperatur auf 180 C ansteigen, welche während 8 Stunden aufrechterhal ten wird. Das erzielte Gemisch wird auf 100 C gekühlt, mit 25G Teilen heissem Ätha- nol verdünnt und filtriert.
Der Filterkuchen wird mit 200 Teilen heissem Äthanol dige- riert und filtriert; dieser Vorgang wird so lange wiederholt, bis ein farbloses. Filtrat er halten wird. Dann wird der Filterkuchen zur Beseitigung des Alkohols gründlich mit Was ser gewaschen und schliesslich mit Wasser angeteig-t, um eine annähernd 10 % ige Paste zu erhalten.
Imperial Chemical Industries Limited, London (Great Britain). Process for the production of a new phthaloeyanine derivative. The present invention relates to a process for the production of a new phthalocyanine dye, intermediate product, which is characterized in that copper - tetra - 4 - (in - nitrobenzene -, sulfonylamino)
- phthalocyanine to copper tetra-4- (m-arninohenenzene-sulfonylamino) phthalocyanine. is reduced.
The reduction can be carried out in the manner known for reducing nitro compounds to amino compounds, for example by the action of alkali metal sulfides, hydrogen sulfides, polysulfides, sulfites, bisulfites or hydrosulfites, or with the aid of tin, zinc, or stannous chloride and Perform acid.
The novel phthalocyanine intermediate product obtained according to the invention is a dark, bluish-green, solid product which is insoluble in water, but can be diazotized to form a diazonium compound which can be used for the manufacture of azo dyes.
Example: The 1% paste of copper-tetra-4- (m-nitrobenzene-sulfonylamino) -pht3ialocyanine (obtained in the manner described below) is stirred at 0 ° to 5 ° C. and mixed with 147 parts of concentrated hydrochloric acid from specific weight 1.18 offset.
Then a solution of 160 parts of stannous chloride dihydrate in 200 parts of water is added and the mixture is stirred for 16 hours, the temperature being allowed to rise slowly to 20.degree. The product is filtered and the remaining solid product is washed thoroughly with dilute hydrochloric acid until it no longer contains any tin salts, whereupon it is washed with water and finally with a dilute ammonium hydrogen solution.
Subsequently, washing is continued until the residue is free of ammonia. The copper tetra-4- (m-aminobenzene-sulphonylamino) -phthalocyanine obtained in this way can be dried to give a dark bluish-green product. , but it will advantageously be kept in the form of an aqueous paste for use purposes.
The aqueous paste of the copper tetra-4- (m-nitrobenzenesulfonylamino) phthalocyanine used in this example is prepared as follows: An aqueous paste containing <B> 10.5 </B> parts of copper-tetra-4-aminophthalocyanine The paste is filtered and the filter cake is washed with acetone until it is anhydrous.
The filter cake moist with acetone is then introduced into 178 parts of dry nitrobenzene and the temperature of the mixture of masses thus obtained is increased until the acetone has distilled off. This suspension is then mixed with 50 parts of m-nitrobenzenesulfonyl chloride and the temperature is allowed to rise to 180 ° C., which is maintained for 8 hours. The resulting mixture is cooled to 100 ° C., diluted with 25G parts of hot ethanol and filtered.
The filter cake is digested with 200 parts of hot ethanol and filtered; this process is repeated until a colorless one. Filtrate he will hold. The filter cake is then washed thoroughly with water to remove the alcohol and finally made into a paste with water to obtain an approximately 10% paste.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB249635X | 1945-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH249635A true CH249635A (en) | 1947-07-15 |
Family
ID=10220043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH249635D CH249635A (en) | 1945-03-26 | 1946-03-25 | Process for the production of a new phthalocyanine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH249635A (en) |
-
1946
- 1946-03-25 CH CH249635D patent/CH249635A/en unknown
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