GB397879A - Azo dyestuffs - Google Patents

Azo dyestuffs

Info

Publication number
GB397879A
GB397879A GB3282531A GB3282531A GB397879A GB 397879 A GB397879 A GB 397879A GB 3282531 A GB3282531 A GB 3282531A GB 3282531 A GB3282531 A GB 3282531A GB 397879 A GB397879 A GB 397879A
Authority
GB
United Kingdom
Prior art keywords
acid
amino
pyrazolone
methyl
naphthol
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
GB3282531A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB3282531A priority Critical patent/GB397879A/en
Publication of GB397879A publication Critical patent/GB397879A/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
    • C09B31/00Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/16Trisazo dyes
    • C09B31/22Trisazo dyes from a coupling component "D" containing directive hydroxyl and amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Azo dyes; azo dyes, forming on the material; regenerated celluloses, dyeing.--Trisazo dyes are obtained by coupling a diazotized amine of the benzene or naphthalene series with a 1-(m- or p-amino)-aryl-3-methyl (or 3-carboxy)-5-pyrazolone, diazotizing the resulting aminoazo compound, coupling with a usual middle component, again diazotizing and coupling in acid, neutral or alkaline medium with a naphthol, naphthylamine or aminonaphthol or a sulphonic acid of these or a naphtholcarboxylic acid or an N-substituted naphthylamine or aminonaphthol sulphonic acid, the end component being other than a 1 : 8-aminonaphtholsulphonic acid or an N-acyl derivative thereof when the third component is a 1-amino-2-naphthol ether or a derivative thereof. When the N-substituent contains a diazotizable amino group the trisazo product may be diazotized and coupled with a component in substance or on the fibre. In examples the preparation is described of the following dyestuffs: (1) sulphanilic acid --> 1-(m-amino)-phenyl-3-methyl-5-pyrazolone --> 2 : 5-dimethoxyaniline --> (in ammonia solution) 1-p-(amino) benzoylamino-8-naphthol-4-sulphonic acid, which dyes cotton clear blueish green and may be diazotized and developed on the fibre with 1-phenyl-3-methyl-5-pyrazolone to give clear yellowish green shades, (2) sulphanilic acid --> 1-(m-amino)-phenyl-3-methyl-5-pyrazolone --> 1-amino-2-ethoxynaphthalene-6-sulphonic acid --> 2-naphthol-3 : 6-disulphonic acid, which dyes cotton and viscose artificial silk blueish green, (3) 2-naphthylamine-4 : 8-disulphonic acid --> 1-(m-amino)-phenyl-3-methyl-5-pyrazolone --> 1-naphthylamine-2-thioglycollic acid --> (in ammonia solution) 2 - (p - amino) - benzoylamino - 5 -naphthol - 7-sulphonic acid, which dyes cotton blueish green and may be diazotized and developed on the fibre with acetoacetic o-chloranilide to give clear yellowish green shades fast to washing, (4) the aminodisazo dyestuff in (3) --> (in pyridine solution) 2-methylaminonaphthalene-7-sulphonic acid, which dyes cotton and viscose artificial silk blue-green, (5)2 : 5-dichloraniline-4 - sulphonic acid --> 1-(m-amino) phenyl - 3 methyl - 5 - pyrazolone --> 1 - amino - 2-ethoxynaphthalene - 6 - sulphonic acid --> (in ammoniacal pyridine solution) 2-phenylamino-5-naphthol-7-sulphonic acid, which dyes cotton greenish blue, (6) 2-naphthylamine-8-sulphonic acid --> 1 - (p-amino) phenyl - 3 - methyl - 5 - pyrazolone --> 1-naphthylamine- 7 -sulphonic acid --> (in ammoniacal pyridine solution) 1-(o-chloro) benzoylamino-8-naphthol-3 : 6-disulphonic acid, which dyes cotton yellowish green, (7) m-aminobenzoic acid --> 1-(p-amino)phenyl-5-pyrazolone-3-carboxylic acid --> 1-naphthylamine --> (in ammonia solution) 1-amino-8-naphthol-2 : 4-disulphonic acid, which dyes cotton green, (8) sulphanilic acid --> 1-(p-aminosulphophenyl-3-methyl-5-pyrazolone --> 2 : 5-dimethoxyaniline --> (in ammoniacal pyridine solution) 1-acetylamino-8-naphthol-3 : 6-disulphonic acid, which dyes cotton clear green, (9) metanilic acid --> 1-(4<1>-amino-1<1>-naphthyl)-3-methyl-5-pyrazolone --> 1-amino-2-ethoxy-naphthalene-6-sulphonic acid --> (in ammoniacal pyridine solution) 2 - phenylamino-5-naphthol-7-sulphonic acid, which dyes cotton blue-green, (10) metanilic acid --> 1-(m-amino)-phenyl-3-methyl-5-pyrazolone --> 1-amino-2-ethoxynaphthalene-6-sulphonic acid --> (in ammoniacal pyridine solution) 1 : 5-amino-naphthol, which dyes cotton blue-green, (11) sulphanilic acid --> 1- (p-amino) phenyl-3-methyl-5-pyrazolone --> 1-naphthylamine-2-thioglycollic acid --> 1-naphthol, which dyes cotton blue-green, (12) the aminodisazo dyestuff in (3) --> 2 : 3-oxynaphthoic acid, which dyes cotton blue-green. 1 - (p-Aminosulpho) phenyl-3-methyl - 5 - pyrazolone is obtained by sulphonating 1-(p-amino)-phenyl - 3 - methyl - 5 - pyrazolone with chlorosulphonic acid in tetrachlorethane; the sulpho group is probably in the 3<1>-position. 1 -(4<1>-Amion-1<1>-naphthyl- 3 - methyl - 5 - pyra-zolone is obtained by reducing diazotized 4-nitro-1-naphthylamine to the nitrohydrazine, condensing the product with acetoacetic ester and reducing the nitro group.
GB3282531A 1931-11-26 1931-11-26 Azo dyestuffs Expired GB397879A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3282531A GB397879A (en) 1931-11-26 1931-11-26 Azo dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3282531A GB397879A (en) 1931-11-26 1931-11-26 Azo dyestuffs

Publications (1)

Publication Number Publication Date
GB397879A true GB397879A (en) 1933-08-28

Family

ID=10344553

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3282531A Expired GB397879A (en) 1931-11-26 1931-11-26 Azo dyestuffs

Country Status (1)

Country Link
GB (1) GB397879A (en)

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