GB578537A - Process for the preparation of metallisable polyazo dyestuffs - Google Patents

Process for the preparation of metallisable polyazo dyestuffs

Info

Publication number
GB578537A
GB578537A GB11971/44A GB1197144A GB578537A GB 578537 A GB578537 A GB 578537A GB 11971/44 A GB11971/44 A GB 11971/44A GB 1197144 A GB1197144 A GB 1197144A GB 578537 A GB578537 A GB 578537A
Authority
GB
United Kingdom
Prior art keywords
dyestuff
product
hydroxybenzene
coupling
acid
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
GB11971/44A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB578537A publication Critical patent/GB578537A/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
    • C09B35/38Trisazo dyes ot the type
    • C09B35/40Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound

Landscapes

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

Abstract

Metallizable polyazo dyestuffs are manufactured by reacting on one molecular proportion of resorcinol in either order with, on the one hand, one molecular proportion of a diazotized aminoazo dyestuff of the general formula <FORM:0578537/IV/1> in which A is the radicle of a diazo- or coupling component, which may contain azo groups but must not contain either diazotizable amino groups or carbon atoms capable of coupling, and in which the nucleus B must contain a hydroxyl group in one of the o-positions to the amino group and may contain other substituents, and, on the other hand, one molecular proportion of an intermediate compound obtainable by coupling one end of a tetrazotized 4 : 41-diaminodiaryl with a 1-hydroxybenzene-2-carboxylic acid. The aminoazo dyestuffs employed as starting materials may be obtained by coupling a diazo compound, which may contain azo groups, but neither free nor acylated amino groups nor carbon atoms capable of coupling, with a 1-hydroxy-2-acylaminobenzene with a free 4-position, or with a derivative thereof, and saponifying the acylamino group; or by coupling a 1-diazo-3-acylamino-4-hydroxybenzene, or a derivative thereof, with a coupling component containing only a single group enabling coupling to take place and containing no free or acylated amino group, and subsequently saponifying. The products of the invention dye cotton and regenerated cellulose brown shades, the fastness of which may be improved by the action of reagents furnishing metals. In examples: (1) the aminoazo dyestuff produced by saponifying the dyestuff naphthionic acid --> o-acetylaminophenol is diazotized and coupled with resorcinol, and the product is coupled with the intermediate product from tetrazotized benzidine and salicylic acid; the product dyes cotton red-brown shades, becoming more violetty on treatment with copper sulphate; (2) the o-acetylaminophenol in (1) is replaced by 1-methyl-3-acetylamino-4-hydroxybenzene, the product dyeing cotton red-brown shades becoming brown on treatment with copper salts; (3) the naphthionic acid in (1) is replaced by the monoazo dyestuff of the formula <FORM:0578537/IV/2> to yield a pentakisazo dye which dyes cotton reddish-brown shades, becoming violetty-brown on treatment with copper salts; (4) the aminoazo dyestuff obtained by saponifying the dyestuff sulphanilic acid --> o-acetylaminophenol is diazotized and coupled with resorcinol, and the product is coupled with the intermediate product from tetrazotized 3 : 31-tolidine and 1-methyl-2-hydroxy-3-benzoic acid; the product has similar properties to that of (1); (5) the o-acetylaminophenol of (1) is replaced by 1 - acetylamino - 2 - hydroxybenzene - 5 - sulphonic acid, the product dyeing cotton brown shades becoming violetty on treatment with copper sulphate; (6) the aminoazo dyestuff of (1) is replaced by that produced by saponifying the dyestuff 1-amino-3-acetylamino-4- hydroxybenzene --> 1-phenyl-3-methylpyrazolone-41-sulphonic acid; the product dyes cotton yellowish-brown shades, the fastness to light and to washing being improved by treatment with copper salts. The properties of further tetrakisazo and pentakisazo dyestuffs are shown in a table. 1-Acetylamino-2-hydroxybenzene-5-sulphonic acid is obtainable by stirring an aqueous solution of sodium 1-amino-2-hydroxybenzene-5-sulphonate with acetic anhydride at room temperature. The Specification as open to inspection under Sect. 91 comprises also in the table dyestuffs obtained by replacing the aminoazo dyestuff in (1) above by dyestuffs of the formul <FORM:0578537/IV/3> and <FORM:0578537/IV/4> This subject-matter does not appear in the Specification as accepted.
GB11971/44A 1943-07-02 1944-06-23 Process for the preparation of metallisable polyazo dyestuffs Expired GB578537A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH578537X 1943-07-02

Publications (1)

Publication Number Publication Date
GB578537A true GB578537A (en) 1946-07-02

Family

ID=4521351

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11971/44A Expired GB578537A (en) 1943-07-02 1944-06-23 Process for the preparation of metallisable polyazo dyestuffs

Country Status (1)

Country Link
GB (1) GB578537A (en)

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