GB391626A - Manufacture of primary disazo-dyestuffs - Google Patents

Manufacture of primary disazo-dyestuffs

Info

Publication number
GB391626A
GB391626A GB1567732A GB1567732A GB391626A GB 391626 A GB391626 A GB 391626A GB 1567732 A GB1567732 A GB 1567732A GB 1567732 A GB1567732 A GB 1567732A GB 391626 A GB391626 A GB 391626A
Authority
GB
United Kingdom
Prior art keywords
chloro
aminobenzene
sulpho
acid
sulphanilide
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
GB1567732A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Priority to GB1567732A priority Critical patent/GB391626A/en
Publication of GB391626A publication Critical patent/GB391626A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B33/00Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02Disazo dyes
    • C09B33/08Disazo dyes in which the coupling component is a hydroxy-amino compound
    • C09B33/10Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Developing Agents For Electrophotography (AREA)

Abstract

Azo dyes.--Primary disazo dyes are obtained by coupling 1 mol of a 1 : 8-aminonaphthol-sulphonic acid in an acid medium with 1 mol. of a diazotized aminoarylsulphonamide, other than an o-oxyaminoarylsulphonamide and thereafter coupling the monoazo product in an alkaline medium with 1 mol. of any diazo component. The sulphonamide group may be substituted by one or two hydrocarbon residues or substituted hydrocarbon residues. The products dye wool and silk reddish blue to greenish blue and blue-black shades and are well absorbed even from a neutral Glauber salt bath. The production of the following dyestuffs is described in examples: (1) 1-chloro-2-aminobenzene-4-sulphanilide --> (acid) 1 : 8-aminonaphthol-3 : 6-disulphonic acid (alkaline) \sM 1-methyl-4-aminobenzene-2-sulphanilide; (2) 1-chloro - 2 - aminobenzene - 4 - sulphanilide --> (acid) 1 : 8-aminonaphthol-3 : 6-disulphonic acid (alkaline) \sM 4-aminophenol-p-toluene-sulphonic ester; (3) 1-chloro-4-aminobenzene-2-sulpho-N-ethylanilide --> (acid) 1 : 8-aminonaphthol-3 : 6-disulphonic acid (alkaline) \sM 2-amino - 2<1> - methyldiphenyl ether. A table is also given showing the shades obtainable on wool from an acid bath containing dyestuffs produced according to the invention from various components, the following components being specified in addition to those above referred to: (a) as aminoarylsulphonamides diazotized and coupled in acid medium, 1-chloro-2-aminobenzene-4-sulphamide, 1 - chloro - 2 - aminobenzene - 4 - sulphodimethylamide, 1 - methyl 4-amino-benzene 2-sulphanilide, aniline-3-sulphanilide, 1-chloro - 2 - aminobenzene - 4 - sulpho - 2<1> - anisidide, 1 - chloro - 2 - aminobenzene - 4 - sulpho-monobenzylamide, 1-chloro-2- aminobenzene - 4 - sulpho - 4<1> - toluidide, 1 - chloro - 2 - aminobenzene - 4 - sulpho-N-ethylanilide, 1 - chloro - 4 - aminobenzene - 2-sulphanilide, 1-methoxy - 2 - aminobenzene - 4-sulphanilide, 2-amino-4<1>-methyldiphenylsulphone - 4 - sulpho - N - ethylanilide, 1-chloro-2-aminobenzene - 4 - sulphanilide - 3<1> - sulphonic acid; (b) as components diazotized and coupled in alkaline medium, 4-chloro-2-aminodiphenyl ether, 2-chloraniline, 4-aminodiphenyl ether, 1- or 2-naphthylamine, 2-aminodiphenyl ether - 4 - sulphonic acid; (c) as 1 : 8-aminonaphtholsulphonic acids, 1 : 8-aminonaphthol - 4 - sulphonic acid and 1 : 8-aminonaphthol-4 : 6-disulphonic acid. Specifications 15725/91, 9894/93, 15269/93, 12529/95, [all in p Class 2, Acids and salts, Organic &c.], and 12205/09, [Class 2 (iii), Dyes &c.], are referred to. 1 - Chloro - 1 - aminobenzene - 4 - sulphamide and the corresponding sulphanilide, sulphodimethylamide, sulpho-2<1>-anisidide, sulpho-4<1>-toluidide, sulpho-N-ethylanilide and sulphanilide-3<1>-sulphonic acid are obtained by reduction of the products of condensation of 2-nitro-1-chlorobenzene-4-sulphochloride with ammonia, aniline, dimethylamine, 2<1>-anisidine, 4<1>-toluidine, monoethylaniline and metanilic acid respectively. 1 - Chloro - 2 - aminobenzene - sulphomonobenzylamide is obtained by condensation of 2 - nitro - 1 - chlorobenzene - 4 - sulphochloride with ammonia followed by condensation of the product with benzyl chloride and reduction of the nitro group. 1 - Chloro - 4 - aminobenzene - 2 - sulpho - N - ethylanilide is obtained by reduction of 1-chloro-4-nitrobenzene-2-sulpho-N-ethylanilide. 1 - Chloro - 4 - aminobenzene - 2 - sulphanilide is obtained by reduction of the condensation product of 4-nitro-1-chlorobenzene-2-sulphochloride with aniline. 2 - Amino - 4<1> - methyldiphenylsulphone - 4 - sulpho - N - ethylanilide is obtained by reduction of the condensation product of 1-chloro-2-nitrobenzene-4-sulpho-N-ethylanilide, obtainable as above, with p-toluenesulphinic acid.
GB1567732A 1932-06-02 1932-06-02 Manufacture of primary disazo-dyestuffs Expired GB391626A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1567732A GB391626A (en) 1932-06-02 1932-06-02 Manufacture of primary disazo-dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1567732A GB391626A (en) 1932-06-02 1932-06-02 Manufacture of primary disazo-dyestuffs

Publications (1)

Publication Number Publication Date
GB391626A true GB391626A (en) 1933-05-04

Family

ID=10063428

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1567732A Expired GB391626A (en) 1932-06-02 1932-06-02 Manufacture of primary disazo-dyestuffs

Country Status (1)

Country Link
GB (1) GB391626A (en)

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