GB653356A - Process for the manufacture of halogenated derivatives of the naphthoquinoneimine series - Google Patents
Process for the manufacture of halogenated derivatives of the naphthoquinoneimine seriesInfo
- 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
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.
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)
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 |
-
1948
- 1948-06-18 GB GB1646048A patent/GB653356A/en not_active Expired
Cited By (2)
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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