GB480693A - Manufacture of oxazines of the anthraquinone series - Google Patents

Manufacture of oxazines of the anthraquinone series

Info

Publication number
GB480693A
GB480693A GB2332036A GB2332036A GB480693A GB 480693 A GB480693 A GB 480693A GB 2332036 A GB2332036 A GB 2332036A GB 2332036 A GB2332036 A GB 2332036A GB 480693 A GB480693 A GB 480693A
Authority
GB
United Kingdom
Prior art keywords
amino
sodium
sulphonate
aminophenol
sulphonic acid
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
GB2332036A
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 GB2332036A priority Critical patent/GB480693A/en
Publication of GB480693A publication Critical patent/GB480693A/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
    • C09B5/44—Azines of the anthracene series
    • C09B5/60—Thiazines; Oxazines

Landscapes

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

Abstract

Oxazines of the anthraquinone series are made by reacting a 1-halogenanthraquinone-2-sulphonic acid which may contain further substituents, radicals or atom groups in the anthraquinone nucleus, with a compound containing an amino group and a hydroxyl group in o-positions to each other, in the presence of an acid-binding agent, and advantageously in presence of copper or a copper compound, and if desired, sulphonating the products obtained. The reaction may take place in an aqueous or alcoholic medium, at temperatures between room temperature and 100 DEG C. and aminohydroxy compounds specified are those of the benzene, naphthalene, or anthraquinone series. The products dye wool or cotton blue or violet tints. In examples, the potassium salt of 1-iodanthraquinone-2-sulphonic acid is reacted in aqueous solution in presence of sodium carbonate and cuprous chloride with (1) o-aminophenol, followed by sulphonation; (2) sodium 2-hydroxy-3-amino-5-sulphobenzoate; (3) 3.5.6-trichloro-2-aminophenol-4-sulphonic acid; (4) 3.4.5.6-tetrachloro-2-aminophenol; (5) 6-chloro-2-aminophenol-4-sulphonic acid; (6) 4-chloro-2-aminophenol-6-sulphonic acid; (7) 3-amino - 4 - hydroxy - 1 - methylbenzene - 5-sulphonic acid; (8) 2-amino-4-acetaminophenol-6-sulphonic acid; and (9) 3-amino-4-hydroxybenzophenone-21-carboxylic acid, followed by ring-closure of the benzophenone part of the molecule by sulphuric acid to give a dianthraquinone oxazine which may also be obtained by condensing potassium 1-bromo (or iodo)-anthraquinone-2-sulphonate with 1-amino-2-hydroxyanthraquinones; (10) the potassium salt of 1-iodo-4-phenylaminoanthraquinone-2-sulphonic acid is condensed with 3.4.5.6-tetrachloro-2-aminophenol; (11) potassium 1-iodoanthraquinone-2.6-disulphonate is condensed with 5-amino-2.4-dihydroxybenzoic acid, (12) sodium-1 - bromanthraquinone-2-sulphonate is condensed with sodium 2-amino-4-nitrophenol-6-sulphonate or sodium 2-amino-6-nitrophenol-4-sulphonate, potassium 1-iodoanthraquinone-2-sulphonate is condensed with (13) sodium 3 - amino - 4 - hydroxydiphenylsulphone - 31 - sulphonate; and (14) sodium 1-hydroxy-2-aminonaphthalene-4-sulphonate; (15) sodium 1-bromanthraquinone-2.4-disulphonate is reacted with 2-amino-4-acetaminophenol; (16) sodium 1 - iodo - 4 - bromanthraquinone - 2 - sulphonate is reacted with sodium - 2 - amino - 4 - acetaminophenol-6-sulphonate; (17) sodium 1-amino-4-bromanthraquinone-3-sulphonate is condensed with o-aminophenol.
GB2332036A 1936-08-25 1936-08-25 Manufacture of oxazines of the anthraquinone series Expired GB480693A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2332036A GB480693A (en) 1936-08-25 1936-08-25 Manufacture of oxazines of the anthraquinone series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2332036A GB480693A (en) 1936-08-25 1936-08-25 Manufacture of oxazines of the anthraquinone series

Publications (1)

Publication Number Publication Date
GB480693A true GB480693A (en) 1938-02-25

Family

ID=10193694

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2332036A Expired GB480693A (en) 1936-08-25 1936-08-25 Manufacture of oxazines of the anthraquinone series

Country Status (1)

Country Link
GB (1) GB480693A (en)

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