GB896681A - Cationic mono-azo dyes, their production and their application - Google Patents

Cationic mono-azo dyes, their production and their application

Info

Publication number
GB896681A
GB896681A GB16955/60A GB1695560A GB896681A GB 896681 A GB896681 A GB 896681A GB 16955/60 A GB16955/60 A GB 16955/60A GB 1695560 A GB1695560 A GB 1695560A GB 896681 A GB896681 A GB 896681A
Authority
GB
United Kingdom
Prior art keywords
condensing
carbon atoms
dyes
coupling
compound
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
GB16955/60A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB896681A publication Critical patent/GB896681A/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
    • C09B56/00Azo dyes containing other chromophoric systems
    • C09B56/16Methine- or polymethine-azo dyes
    • 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
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14Styryl dyes
    • C09B23/143Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The invention comprises dyes of formula <FORM:0896681/IV (c)/1> where Q is the radical of an azo coupling component free from sulpho and/or carboxy groups, X and Y are H, Cl, Br, OH, MeO, EtO or Alk of 1-4 carbon atoms, the ethylenic link is attached to the benzene ring m- or pto the azo bridge, A- is a water-solubilizing anion and R is a cationic radical of a quaternised heterocyclic compound having at least one N-atom and not more than 9 carbon atoms in its cyclic skeleton. The dyes are made by methods which involve forming either the ethylene link or the azo bridge first. Thus they may be made by condensing a m- or p-acetamidobenzaldehyde with a quaternised heterocyclic compound having an Me group in 2 or 4 position relative to the N atom, hydrolysing the acylamido group and diazotising and coupling; by condensing a m- or p-nitrobenzaldehyde with 1-methyl-2 or 4-picolinium methosulphate, or corresponding compound, reducing to an amino compound, diazotising and coupling; by condensing an appropriate azo benzaldehyde with a quaternised heterocyclic nitrogen compound which has a methyl group in the 2 or 4 position or with a Fischer's base in the presence of an acid, or by diazotising an aminobenzaldehyde, coupling with an appropriate component and condensing with a quaternised heterocyclic nitrogen base. Representive of specified components corresponding to Q are p-cresol, resorcinol, the xylenols, 2,4-quinoline-diol, aniline, o-chloraniline, N,N-diethyl - m - toluidine, 3 - (N - methylanilino) - propionitrile, 1 - naphthylamine, diphenyl - amine, 1, 2 - dimethylindole, 1 - phenyl - 3 - methyl-5-pyrazolone and acetoacetanilide. Pyridinium, trimethyl-indoleninium, isoquinolinium, quinoxalinium and benzazolium are representative of values specified for R with radicals such as benzyl and alkyl radicals of 1-4 carbon atoms attached to the quaternary nitrogen atom. The R heterocyclics may contain substituents such as hydrogen, alkyl of 1-4 carbon atoms, Cl, Br, OH, MeO and EtO. A- is represented as Cl, Br, I, phosphate, acetate, methosulphate and p-toluene-sulphonate. Th dyes colour acidmodified acrylic and polyester fibres being applied from an aqueous bath, preferably at pH 4-6. Examples are provided of the preparation of the dyes and their use in colouring processes. Red, yellow and brown shades are obtained.
GB16955/60A 1959-06-09 1960-05-13 Cationic mono-azo dyes, their production and their application Expired GB896681A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US896681XA 1959-06-09 1959-06-09

Publications (1)

Publication Number Publication Date
GB896681A true GB896681A (en) 1962-05-16

Family

ID=22218935

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16955/60A Expired GB896681A (en) 1959-06-09 1960-05-13 Cationic mono-azo dyes, their production and their application

Country Status (2)

Country Link
CH (1) CH651560D (en)
GB (1) GB896681A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4754021A (en) * 1984-08-22 1988-06-28 Ciba-Geigy Corporation Methine-azo compounds containing cyclic ammonium groups

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4754021A (en) * 1984-08-22 1988-06-28 Ciba-Geigy Corporation Methine-azo compounds containing cyclic ammonium groups
US4847364A (en) * 1984-08-22 1989-07-11 Moeckli Peter Methine-azo compounds containing cyclic cationic ammonium groups and open-chain coupling components
US4883866A (en) * 1984-08-22 1989-11-28 Ciba-Geigy Corporation Methine-azo compounds containing cyclic cationic ammonium groups

Also Published As

Publication number Publication date
CH651560D (en)

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