GB470079A - Improvements in the manufacture and production of dyestuffs - Google Patents

Improvements in the manufacture and production of dyestuffs

Info

Publication number
GB470079A
GB470079A GB378636A GB378636A GB470079A GB 470079 A GB470079 A GB 470079A GB 378636 A GB378636 A GB 378636A GB 378636 A GB378636 A GB 378636A GB 470079 A GB470079 A GB 470079A
Authority
GB
United Kingdom
Prior art keywords
chloride
phthalodinitrile
treated
heated
cuprous
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
Application number
GB378636A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB378636A priority Critical patent/GB470079A/en
Publication of GB470079A publication Critical patent/GB470079A/en
Expired legal-status Critical Current

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
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0671—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having halogen atoms linked directly to the Pc skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Chlorinated and brominated phthalocyanines containing more than one halogen atom per molecule are obtained by heating o-dinitriles of aromatic dicarboxylic acids or compounds capable of conversion into them, viz. phthalic imides or diamides and o-cyano-benzamides, with chlorinating or brominating agents containing no metal, such as free chlorine or bromine, sulphuryl chloride or chlorsulphonic acid. Condensing agents such as the anhydrous halides of iron, chromium, copper, aluminium and the metals of the 5th group may also be present, and metals capable of entering into the dyestuff or acting as halogen transferers, such as iron chips, copper or zinc powder. Diluents such as aromatic nitro-hydrocarbons and aliphatic or aromatic halogen-hydrocarbons may be used and increased pressure is advantageous. In the examples: (1) phthalodinitrile is treated with bromine in nitrobenzene solution, and then with cuprous chloride and pyridine; (2) cuprous bromide or chloride, or cupric chloride, is added to phthalodinitrile in nitrobenzene and the mixture is heated with bromine; (3) bromine is added to a mixture of phthalodinitrile and aluminium chloride in nitrobenzene; (4) bromine in nitrobenzene is added to a mixture of phthalodinitrile, nitrobenzene and zinc chloride, oxide or acetate; (5) in the process of the previous example, 4-chloro-phthalodinitrile is used as starting material; (6) phthalodinitrile dissolved in trichlorbenzene is treated with chlorine in the presence of the double compound of carbamic acid chloride with zinc chloride or aluminium chloride; (7) phthalodinitrile, cuprous chloride and pyridine in trichlorbenzene solution are treated with chlorine; (8) chlorine under pressure is allowed to act on phthalodinitrile, copper powder, iodine and o-dichloro-benzene; (9) phthalodinitrile, zinc dust, sodium chloride and anhydrous iron chloride are treated with chlorine under pressure; (10) phthalodinitrile, aluminium chloride, sodium chloride and potassium chloride are treated with chlorine under pressure; (11) phthalodinitrile is heated with phosphorus oxychloride in presence of cuprous chloride, zinc chloride, aluminium chloride, or ferric chloride; (12) phthalodinitrile or o-cyanobenzamide is heated with sulphuryl chloride or sulphur monochloride; (13) phthalodinitrile is heated with phosphorus oxychloride; (14) phthalodinitrile and iodine in carbon tetrachloride are heated with chlorine under pressure; (15) 3 : 4-dicyandiphenyl with nitrotoluene and iodine is treated with sulphur monochloride and then with cuprous dichloride and pyridine; (16) phthalodinitrile is heated with cuprous chloride, antimony trisulphide and sulphuryl chloride. The products may be finely divided by dissolving in concentrated sulphuric acid and pouring on to ice, or by grinding with salt. Specification 410,814 and the Journal of the Chemical Society, 1934, p. 1016 et seq. are referred to.
GB378636A 1936-02-07 1936-02-07 Improvements in the manufacture and production of dyestuffs Expired GB470079A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB378636A GB470079A (en) 1936-02-07 1936-02-07 Improvements in the manufacture and production of dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB378636A GB470079A (en) 1936-02-07 1936-02-07 Improvements in the manufacture and production of dyestuffs

Publications (1)

Publication Number Publication Date
GB470079A true GB470079A (en) 1937-08-09

Family

ID=9764889

Family Applications (1)

Application Number Title Priority Date Filing Date
GB378636A Expired GB470079A (en) 1936-02-07 1936-02-07 Improvements in the manufacture and production of dyestuffs

Country Status (1)

Country Link
GB (1) GB470079A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3414583A (en) * 1964-06-25 1968-12-03 Imp Smelting Corp Ltd Copper hexadecafluorophthalocyanine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3414583A (en) * 1964-06-25 1968-12-03 Imp Smelting Corp Ltd Copper hexadecafluorophthalocyanine

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