GB569771A - Disazo dyestuffs - Google Patents

Disazo dyestuffs

Info

Publication number
GB569771A
GB569771A GB1837443A GB1837443A GB569771A GB 569771 A GB569771 A GB 569771A GB 1837443 A GB1837443 A GB 1837443A GB 1837443 A GB1837443 A GB 1837443A GB 569771 A GB569771 A GB 569771A
Authority
GB
United Kingdom
Prior art keywords
acid
amino
aminobenz
cyclohexyl
alkaline
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
GB1837443A
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 GB1837443A priority Critical patent/GB569771A/en
Publication of GB569771A publication Critical patent/GB569771A/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

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

Abstract

Disazo dyes are made by coupling, in acid medium, one molecular proportion of a diazotised primary arylamine of the benzene or naphthalene series which contains at least one halogen atom or one of the groups carboalkoxy, carboxy and carbamyl, wherein the hydroxy of the carboxy and the hydrogen of the carbamyl group may optionally be replaced by hydrocarbon residues or substituted hydrocarbon residues, but which is devoid of nitro, acidylamino, aminosulphonyl, sulpho and sulphone groups, with 1-amino-8-naphthol-3.6- or 4.6-disulphonic acid, and coupling, in alkaline medium, with the resulting monoazo compound, one molecular proportion of a diazotised amine of the formula X-CO-NY-R-NH2, wherein R represents a p-phenylene residue which may be substituted by, e.g. methyl or methoxy, but which contains no amyloxy or sulphonic acid substituent, X represents a monochloro- or monobromo-methyl group and Y represents an alkyl group of less than 7 carbon atoms or a cycloalkyl group. In examples, the following dyes are made: o-chloroaniline --> (acid) H-acid (alkaline) \sM 4-amino-1-N-cyclohexyl-o -chloroacetanilide, m-aminoacetophenone --> (acid) H-acid (alkaline) \sM 4-amino-1-N-cyclohexyl-o -chloro- or bromo-acetanilide, 4-aminobenz-N-ethylanilide or m-aminobenzoic acid --> (acid) H-acid (alkaline) \sM 4-amino-1-N-cyclohexyl - o - chloroacetanilide, n - butyl, n-aminobenzoate --> (acid) H-acid (alkaline) \sM 4-amino-1-N-cyclohexyl-o -chloroacetanilide, 4-aminobenz-N-benzylanilide --> (acid) H-acid (alkaline) \sM 4-amino-1-N-ethyl-o -chloro- or bromo-acetanilide or 4-amino-1-N-n-butyl - o - chloroacetanilide and 2.5 - dichloroaniline --> (acid) K-acid (alkaline) \sM 4-amino - 1 - N - cyclohexyl - o - chloroacetanilide. Additional diazo components specified are: p-aminobenzoic acid, 4-chloro-2-aminobenzoic acid, m- or p-chloroaniline, o-, m- or p-bromoaniline, 2.4-dichloroaniline, 4-chloro-2-aminoanisole, 5-chloro-2-aminotoluene, 3- or 4-aminobenzanilide, 3 - aminobenz - N - ethylanilide, 4-aminobenz-m-toluidide, N -3-aminobenz-N-b -hydroxyethylanilide, 3- or 4-aminobenzoyldiphenylamine, 4 - aminobenz - N - cyclohexyl - anilide, N-4-aminobenzoyl-N-ethyl-21-aminotoluene, n - butyl, p - aminobenzoate, 3- or 4-aminobenzoyl - N - ethyl -a - naphthylamine, 4-amino-N.N-dimethylbenzamide and p-amino-aceto- or benzo-phenone; 4-amino-1-N-isopropyl- or (p - methylcyclohexyl) - o - chloroacetanilide and 5 - amino - 2 - N - cyclohexyl-o -chloroacet-toluidide. The dyes are suitable for dyeing animal fibres, wool and silk being specified. The Provisional Specification describes also the production of dyes wherein R, in the above formula, represents a m- or p-phenylene residue which may be substituted by, e.g. methyl, methoxy or (except para to the amino group) sulphonic acid groups, but which contains no amyloxy substituent, X represents a monochloro- or monobromo-alkyl radical of not more than three carbon atoms and Y represents hydrogen, alkyl of less than seven carbon atoms, cycloalkyl, aralkyl, alkoxyalkyl or aryl, and wherein the middle component may be any 1-amino-8-naphthol sulphonic acid having the 2- and 7-positions free. N - 3 - Aminobenz - N - b - hydroxyethylanilide is obtained by reacting m-nitrobenzoyl chloride with N-b -hydroxyethylaniline and reducing the nitro group. 4-Aminobenz-N-benzylanilide is obtained by reacting N-benzylaniline with p-nitrobenzyl chloride and reducing the nitro group. N - 4 - Aminobenzoyl - N - ethyl - 21 - aminotoluene is obtained by reacting N-ethyl-o-toluidine with p-nitrobenzoyl chloride and reducing the nitro group. 4 - Amino - N : N - dimethylbenzamide is obtained by reacting p-nitrobenzyl chloride with dimethylamine and reducing the nitro group.
GB1837443A 1943-12-02 1943-12-02 Disazo dyestuffs Expired GB569771A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1837443A GB569771A (en) 1943-12-02 1943-12-02 Disazo dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1837443A GB569771A (en) 1943-12-02 1943-12-02 Disazo dyestuffs

Publications (1)

Publication Number Publication Date
GB569771A true GB569771A (en) 1945-06-07

Family

ID=10111361

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1837443A Expired GB569771A (en) 1943-12-02 1943-12-02 Disazo dyestuffs

Country Status (1)

Country Link
GB (1) GB569771A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1247511B (en) * 1957-07-25 1967-08-17 Cassella Farbwerke Mainkur Ag Process for the preparation of disazo dyes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1247511B (en) * 1957-07-25 1967-08-17 Cassella Farbwerke Mainkur Ag Process for the preparation of disazo dyes

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