GB653356A - Process for the manufacture of halogenated derivatives of the naphthoquinoneimine series - Google Patents

Process for the manufacture of halogenated derivatives of the naphthoquinoneimine series

Info

Publication number
GB653356A
GB653356A GB1646048A GB1646048A GB653356A GB 653356 A GB653356 A GB 653356A GB 1646048 A GB1646048 A GB 1646048A GB 1646048 A GB1646048 A GB 1646048A GB 653356 A GB653356 A GB 653356A
Authority
GB
United Kingdom
Prior art keywords
reacting
intermediate product
naphthazarin intermediate
naphthazarin
naphthoquinoneimines
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
GB1646048A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Priority to GB1646048A priority Critical patent/GB653356A/en
Publication of GB653356A publication Critical patent/GB653356A/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
    • C09B13/00—Oxyketone dyes
    • C09B13/02—Oxyketone dyes of the naphthalene series, e.g. naphthazarin

Landscapes

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

Abstract

Halogenated naphthoquinoneimines are prepared by halogenating naphthoquinoneimines of the formula: <FORM:0653356/IV (c)/1> which are prepared by reacting the naphthazarin intermediate compound, 5-amino-8-hydroxy - 1,4 - naphthaquinoneimide with aliphatic, cycloaliphatic or aromatic amines, e.g. according to the processes of U.S.A. Specifications 647,370, 668,445, 2,066,119, and 2,135,366. One, two or three amine radicals may be introduced into the naphthazarin intermediate product. Halogenation is preferably carried out in a diluent such as sulphuric or acetic acids, or nitrobenzene in the presence of acid-binding agents, and in ultra-violet light. The products dye acetate silk and nylon greenish-blue shades. In examples, the products obtained by reacting the naphthazarin intermediate product with the following amines are brominated: (1) p-phenetidine; (2) methylamine; (3) ethylamine; (4) hexahydroaniline; (5) aniline; (6) toluidine; (7) p-aminophenol; (8) n-amylamine; (9) aminoethanol; (10) cyclohexylene; (11) 1-phenyl - 3 - amino - 5 - pyrazolone. Also in examples, the products obtained by reacting the naphthazarin intermediate product with (1) aniline and (2) p-aminophenol are chlorinated with sulphuryl chloride.
GB1646048A 1948-06-18 1948-06-18 Process for the manufacture of halogenated derivatives of the naphthoquinoneimine series Expired GB653356A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1646048A GB653356A (en) 1948-06-18 1948-06-18 Process for the manufacture of halogenated derivatives of the naphthoquinoneimine series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1646048A GB653356A (en) 1948-06-18 1948-06-18 Process for the manufacture of halogenated derivatives of the naphthoquinoneimine series

Publications (1)

Publication Number Publication Date
GB653356A true GB653356A (en) 1951-05-16

Family

ID=10077731

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1646048A Expired GB653356A (en) 1948-06-18 1948-06-18 Process for the manufacture of halogenated derivatives of the naphthoquinoneimine series

Country Status (1)

Country Link
GB (1) GB653356A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2982596A (en) * 1954-01-15 1961-05-02 Sandoz Ltd N, n'-diarylnaphthoquinone-imines
US3516778A (en) * 1964-06-09 1970-06-23 Clairol Inc Naphthoquinone imine compositions and method for using the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2982596A (en) * 1954-01-15 1961-05-02 Sandoz Ltd N, n'-diarylnaphthoquinone-imines
US3516778A (en) * 1964-06-09 1970-06-23 Clairol Inc Naphthoquinone imine compositions and method for using the same

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