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GB706427A - New disazo dyestuffs - Google Patents

New disazo dyestuffs

Info

Publication number
GB706427A
GB706427A GB1228551A GB1228551A GB706427A GB 706427 A GB706427 A GB 706427A GB 1228551 A GB1228551 A GB 1228551A GB 1228551 A GB1228551 A GB 1228551A GB 706427 A GB706427 A GB 706427A
Authority
GB
United Kingdom
Prior art keywords
methyl
diamino
sulphophenyl
pyrazolone
mols
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
GB1228551A
Inventor
Arthur Howard Knight
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 GB1228551A priority Critical patent/GB706427A/en
Publication of GB706427A publication Critical patent/GB706427A/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
    • C09B35/00Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02Disazo dyes
    • C09B35/039Disazo dyes characterised by the tetrazo component
    • C09B35/28Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—

Landscapes

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

Abstract

N-substituted diaminobenzanilides of the general formula <FORM:0706427/IV (b)/1> (wherein R represents a b -phenoxyethyl group the phenyl group of which carries at least one substituent selected from halogen, alkyl of 1-6 carbon atoms and cycloalkyl, the primary amino groups are in meta- or paraposition to the -CO.NR- bridge, and the nuclei X and Y may carry a further substituent or substituents, e.g. an alkyl or alkoxy group) are prepared by condensing an appropriate m- or p-mononitro-N-(b -phenoxyethyl)-aniline with an appropriate mononitrobenzoyl halide and then reducing the nitro groups. The products, of which many examples are listed, are intermediates for disazo dyestuffs (see Group IV (c)). Specifications 645,594 and 706,426 are referred to.ALSO:The invention comprises the manufacture of disazo dyestuffs by tetrazotizing N-substituted diaminobenzanilides of the general formula <FORM:0706427/IV(c)/1> (wherein R represents a b -phenoxyethyl group the phenyl group of which carries at least one substituent selected from halogen, alkyl of 1-6 carbon atoms and cycloalkyl, the primary amino groups are in meta- or para-position to the -CO.NR-bridge, and the nuclei X and Y may carry a further substituent or substituents, e.g. an alkyl or alkoxy radical) and coupling with two molecular proportions of one or more 1-phenyl-3-methyl-5-pyrazolone-monosulphonic acids, and the products so obtainable (which dye animal fibres such as wool and silk yellow shades from a neutral or weakly acid dyebath, e.g. one containing ammonium acetate). Examples describe the production of the following dyestuffs: (1) 3 : 3\sv-diamino-1\sv-N-b -4"-chlorophenoxyethylbenzanilide \sQ 1 - (4\sv - sulphophenyl)-3-methyl-5-pyrazolone (2 mols); (2) 3 : 3\sv-diamino-6\sv-methyl-1\sv-N-b -2" : 4"-dichlorophenoxyethylbenzanilide \sQ 1 - (2\sv : 5\sv-dichloro-4\sv-sulphophenyl)-3-methyl-5-pyrazolone (2 mols); (3) 3 : 4-diamino-1\sv-N-b -2":4"-dichlorophenoxyethylbenzanilide \sQ the coupling component of (1); (4) and (5) the tetrazo component of (2) 2 mols of 1-(2\sv : 5\sv-dichloro-4\sv-sulphophenyl)- or 1-(3\sv- or 4\sv-sulphophenyl)-3-methyl-5-pyrazolone; (6) 3 : 3\sv-diamino-6\sv-methyl-1\sv-N-b -4"-tert. -butylphenoxyethylbenzanilide \sQ the coupling component of (2); (7) the coupling component of (2) \sM the tetrazo component of (2) --> the coupling component of (1); (8) the tetrazo component of (6) \sQ the coupling component of (1); (9) 3 : 3\sv-diamino-4 : 6\sv-dimethyl-1\sv-N-b -4"-chlorophenoxyethylbenzanilide \sQ 1-(2\sv-chloro-5\sv-sulphophenyl)-3-methyl-5-pyrazolone (2 mols); (10) 3 : 3\sv-diamino-6\sv-methyl-1\sv-N-b -4"-cyclohexylphenoxy ethylbenzanilide \sQ 1-(2\sv-chloro-4\sv-methyl-5\sv-sulphophenyl) -3-methyl-5-pyrazolone (2 mols); (11) 3 : 3\sv-diamino-4 : 6\sv-dimethyl-1\sv-N-b -2\sv : 4"-dichlorophenoxyethylbenzanilide \sQ 1 - (3\sv - sulphophenyl) - 3 - methyl-5-pyrazolone (2 mols); (12) 3 : 4\sv-diamino-1\sv-N-b -4"-cyclohexylphenoxyethylbenzanilide \sQ 1-(4\sv-chloro-2\sv-sulphophenyl) - 3 - methyl - 5 - pyrazolone (2 mols). A table gives the properties of further dyestuffs, the following additional tetrazo components being specified: 3 : 4\sv-diamino-4-methyl-1\sv-N-b -4"-chloro- and -2"-methyl-phenoxyethylbenzanilide, 4:4\sv-and 3:4\sv-diamino-1\sv-N-b -4"-tert.-butylphenoxyethylbenzanilide, 3 : 3\sv-diamino-1\sv-N-b -2": 4"-dichlorophenoxyethylbenzanilide, 4 : 3\sv-diamino-6\sv - methoxy-1\sv-N-b -4"-chlorophenoxyethylbenzanilide and 4 : 4\sv-diamino-1\sv-N-b -4"-chlorophenoxyethylbenzanilide. Lists of still further tetrazo components and further coupling components are given. Specifications 645,594 and 706,426, [Group IV(b)], are referred to.
GB1228551A 1951-05-25 1951-05-25 New disazo dyestuffs Expired GB706427A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1228551A GB706427A (en) 1951-05-25 1951-05-25 New disazo dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1228551A GB706427A (en) 1951-05-25 1951-05-25 New disazo dyestuffs

Publications (1)

Publication Number Publication Date
GB706427A true GB706427A (en) 1954-03-31

Family

ID=10001744

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1228551A Expired GB706427A (en) 1951-05-25 1951-05-25 New disazo dyestuffs

Country Status (1)

Country Link
GB (1) GB706427A (en)

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