GB467971A - Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series - Google Patents

Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Info

Publication number
GB467971A
GB467971A GB3532635A GB3532635A GB467971A GB 467971 A GB467971 A GB 467971A GB 3532635 A GB3532635 A GB 3532635A GB 3532635 A GB3532635 A GB 3532635A GB 467971 A GB467971 A GB 467971A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
acid chloride
phthaloyl
phthaloylcarbazole
group
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
GB3532635A
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 GB3532635A priority Critical patent/GB467971A/en
Publication of GB467971A publication Critical patent/GB467971A/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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/26—Carbazoles of the anthracene series

Abstract

Mono - phthaloylcarbazole mono - carboxylic acid halides, or monocarboxylic acid halides of compounds of the azimino series which are capable of conversion to monophthaloylcarbazoles, are reacted with aminoanthraquinones, the resulting compounds being heated to split off nitrogen and form the carbazoles. The products are vat dyes difficultly soluble in the usual organic solvents and dyeing vegetable fibres fast shades. In examples, 1-amino-5-benzoylaminoanthraquinone is condensed with (1) 1.2 - phthaloylcarbazole -, 4(or 6, 7, or 8)- carboxylic acid chloride, (2) 1.2-phthaloyl-4-bromcarbazole-5 (or 6 or 7)- carboxylic acid chlorides, (3) 1.2-phthaloyl-6-methylcarbazole-4-carboxylic acid chloride, (4) 1.2-phthaloyl-6-chlorcarbazole-4-carboxylic acid chloride, (5) 1.2 - phthaloyl - 6.7 - dichlorocarbazole - 4 - carboxylic acid chloride, (6) 1.2-phthaloyl-6-chlorcarbazole with a carboxylic acid chloride group in the nucleus of the phthaloyl radical para to a ketonic group, and (7) 2.3-phthaloyl-carbazole-8-carboxylic acid chloride; 1-amino-anthraquinone is condensed with (8) 1.2-phthaloylcarbazole-7 (or 8)-carboxylic acid chloride and (9) 1.2-phthaloylcarbazole-7-carboxylic acid chloride is condensed with 1-amino-5 - p - chlorbenzoyl (or 2<1>.5<1> - dichlorbenzoyl) aminoanthraquinone; (10) 1 - anthraquinonyl - azimino - benzene - p - carboxylic acid chloride is condensed with 1-amino-5-benzoylaminoanthraquinone and the product is heated with methyldiphenylamine. Phthaloylcarbazole carboxylic acid chlorides are prepared from phenylaminoanthraquinones which contain a carboxylic ester group and also a nitro or amino group in a position adjacent to the --NH-- group, by reduction (if a nitro group) and diazotization, thus giving anthraquinonyl - azimino - benzene carboxylic acid esters, which may be converted to the phthaloylcarbazole carboxylic esters by heating, and thence to the acid chloride, or converted to the azimino acid chloride.
GB3532635A 1935-12-20 1935-12-20 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series Expired GB467971A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3532635A GB467971A (en) 1935-12-20 1935-12-20 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3532635A GB467971A (en) 1935-12-20 1935-12-20 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Publications (1)

Publication Number Publication Date
GB467971A true GB467971A (en) 1937-06-21

Family

ID=10376460

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3532635A Expired GB467971A (en) 1935-12-20 1935-12-20 Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series

Country Status (1)

Country Link
GB (1) GB467971A (en)

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