GB500471A - Improvements in the manufacture and production of halogenated dyestuffs of the phthalocyanine series - Google Patents
Improvements in the manufacture and production of halogenated dyestuffs of the phthalocyanine seriesInfo
- Publication number
- GB500471A GB500471A GB2150037A GB2150037A GB500471A GB 500471 A GB500471 A GB 500471A GB 2150037 A GB2150037 A GB 2150037A GB 2150037 A GB2150037 A GB 2150037A GB 500471 A GB500471 A GB 500471A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- chlorine
- phthalocyanine
- phthalyl
- antimony
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
500,471. Dyes. JOHNSON, G. W. (I. G. Farbenindustrie Akt.-Ges.) Aug. 4, 1937, No. 21500. Samples furnished. [Class 2 (iii)] Halogenated dyestuffs of the phthalocyanine series are manufactured by treating phthalocyanines with halogenating agents in the presence of organic acid hatides (or compounds yielding them under the reaction conditions) or aromatic compounds which are halogenated in a side chain, e.g. mono- or polybasic carboxylic acid halides and sulphohalides, such as acetyl chloride or bromide, chloracetyl chloride, propiony chloride, oxalyl chloride, benzoyl chloride, or bromide, 2 : 5-dichlorobenzoyl chloride, phthalyl, isophthalyl or terephthalyl chloride, benzenesulphochloride or p-toluenehulphochloride, mixtures of compounds forming acid halides under the reaction conditions, e.g. a mixture of phthalic anhydride, thionyl chloride (or benzotrichloride) and zinc chloride, also benzal chloride, benzotrichloride, 2 : 4- dichlorobenzotrichloride or 2 : 6-dichlorobenzal chloride. The reaction may be carried out at 150-250‹ C. at atmospheric or increased pressure, and, if desired, in the presence of additional diluents, e.g. trichlorobenzene, nitrobenzene or trichloracetic acid, and advantageously in the presence of halogen transferrers, e.g. anhydrous ferrous or ferric chloride, copper chloride, zinc chloride, antimony trichloride or pentachloride or trisulphide. The colour strength of the products may be increased by dissolving them in concentrated sulphuric acid, oleum or chlorsulphonic acid and pouring the solution into water. In examples : (1) chlorine is passed into a heated suspension of copper phthalocyanine and antimony trisulphide in benzene- or p-toluenesulphochloride; (2) the reaction of (1) is carried out in the of 2 : 5- or 3:4- dichlorobenzoyl chloride; (3) a mixture of phthalyl chloride and commercial trichlorobenzene is employed as the diluent; (4) the trichlorobenzene in (3) is replaced by an additional quantity of phthatyl chloride ; the phthalyl chloride may be replaced by isophthalyl or terephthalyl chloride ; (5) chlorine is passed into a heated suspension of metal-free phthalocyanine and antimony trisulphide in phthalyl chloride ; (G) chlorine is passed into a mixture of copper phthalocyanine, zinc chloride and phthalic anhydride with simultaneous addition of thionyl chloride ; (7) chlorine is passed into a heated suspension of copper phthalocyanine and antimony trisulphide in benzotrichloride, 2 : 4-dichlorobenzotrichloride, benzal chloride, 2 : 6-dichlorbenzal chloride or benzyl chloride or its substitution products; (8) bromine is dropped, or led in vapour form into a suspension of metal-free phthalocyanine and antimony trisulphide in phthalyl chloride or benzenesulphochloride ; metal-containing phthalocyanines may be similarly brominated; (9) the reaction of (6) is performed under different conditions; the thionyl chloride may be vaporized and led in with the chlorine ; (10) chlorine is passed and thionyl chloride simultaneously allowed to drop into a mixture of disodium phthalocyanine, phthalic anhydride and antimony trichloride ; metal-free phthalocyanine or magnesium phthalocyanine may be similarly treated ; (11) nickel, zinc or other metal phthalocyanines are treated as in (1); chlorine is pressed into a heated pressure vessel containing copper phthalocyanine, antimony trisulphide and oxalyl chloride ; bromine may be employed instead of chlorine. Samples have been furnished under Sect. 2 (5) of phthalocyanines containing both chlorine and bromine prepared by passing a mixture of chlorine gas and bromine vapour into heated suspensions of (A) copper phthalocyanine and (B) nickel phthalocyanine in phthalyl chloride in the presence of antimony trisulphide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2150037A GB500471A (en) | 1937-08-04 | 1937-08-04 | Improvements in the manufacture and production of halogenated dyestuffs of the phthalocyanine series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2150037A GB500471A (en) | 1937-08-04 | 1937-08-04 | Improvements in the manufacture and production of halogenated dyestuffs of the phthalocyanine series |
Publications (1)
Publication Number | Publication Date |
---|---|
GB500471A true GB500471A (en) | 1939-02-06 |
Family
ID=10163984
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2150037A Expired GB500471A (en) | 1937-08-04 | 1937-08-04 | Improvements in the manufacture and production of halogenated dyestuffs of the phthalocyanine series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB500471A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1200981B (en) * | 1961-04-27 | 1965-09-16 | Basf Ag | Process for the production of a solvent-stable copper phthalocyanine from alphorm |
DE1208841B (en) * | 1959-11-20 | 1966-01-13 | Ciba Geigy | Process for the production of yellowish green chlorine-bromine-phthalocyanines |
-
1937
- 1937-08-04 GB GB2150037A patent/GB500471A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1208841B (en) * | 1959-11-20 | 1966-01-13 | Ciba Geigy | Process for the production of yellowish green chlorine-bromine-phthalocyanines |
DE1200981B (en) * | 1961-04-27 | 1965-09-16 | Basf Ag | Process for the production of a solvent-stable copper phthalocyanine from alphorm |
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