GB587348A - Manufacture of disazo-dyestuffs - Google Patents

Manufacture of disazo-dyestuffs

Info

Publication number
GB587348A
GB587348A GB20046/46A GB2004646A GB587348A GB 587348 A GB587348 A GB 587348A GB 20046/46 A GB20046/46 A GB 20046/46A GB 2004646 A GB2004646 A GB 2004646A GB 587348 A GB587348 A GB 587348A
Authority
GB
United Kingdom
Prior art keywords
nitro
sulphonic acid
aminophenol
acid
dihydroxynaphthalene
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
GB20046/46A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB587348A publication Critical patent/GB587348A/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
    • C09B33/04Disazo dyes in which the coupling component is a dihydroxy or polyhydroxy compound

Landscapes

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

Abstract

Disazo dyestuffs are manufactured by coupling 1 mol. of 1 : 3-dihydroxynaphthalene with 2 mols. of a diazo-compound or 1 mol. of each of two different diazo-compounds which is or are free from azo groups and which contains, or of which at least one contains, a lake-forming group (e.g. a hydroxy, carboxyl, alkoxy or alkoxy-carboxyl group in o-position to the diazo group), and, if desired, treating the product in substance, during its manufacture, in the dyebath or on the fibre with an agent yielding metal. The products may be used for dyeing and printing animal fibres, e.g. wool, silk and especially leather, and vegetable fibres, especially cellulosic fibres. In examples: (1) 4 - nitro - 2 - aminophenol - 6 - sulphonic acid is diazotized and coupled with 1 : 3-dihydroxynaphthalene in the presence of ferric hydroxide, and the resulting iron compound is coupled with diazotized p - nitraniline, 1 - aminonaphthalene-4-sulphonic acid or 41-nitro-4-aminodiphenylamine-21-sulphonic acid; part of the iron may be replaced by another metal, e.g. copper, and the order of coupling may be reversed; (2) a mixture of 4-nitro-2-aminophenol-6-sulphonic acid and 41-nitro-4-aminodiphenylamine-21-sulphonic acid is diazotized and coupled with 1 : 3-dihydroxynaphthalene in the presence of ferric hydroxide and copper hydroxide; (3) the dyestuff from 6-nitro-1-diazo - 2 - naphthol - 4 - sulphonic acid and 1 : 3 - dihydroxynaphthalene is boiled with an aqueous solution of chromium sulphate, and the resulting chromium compound is coupled with diazotized 4-chloroaniline-3-sulphonic acid, 4-nitraniline-2-sulphonic acid or 21- (or 41-) nitro-4-aminodiphenylamine-41- (or 21-) sulphonic acid; alternatively, the disazo dyestuff is prepared first and then chromed, or the chromium may be replaced by other metals, e.g. iron or manganese; (4) the dyestuff 4 : 6-dinitro-2-aminophenol --> 1 : 3-dihydroxynaphthalene \sM 21 - nitro - 4 - aminodiphenylamine - 41 - sulphonic acid (or 1-aminonaphthalene-4-sulphonic acid) is prepared and heated in aqueous solution with copper sulphate (or a mixture of manganese and nickel sulphates) and sodium acetate; (5) the dyestuff 5-nitro-2-aminophenol --> 1 : 3-dihydroxynaphthalene is boiled with a chroming solution containing chromium hydroxide, tartaric acid and caustic soda, and the product is coupled with diazotized sulphanilic acid or aniline-2 : 5-disulphonic acid; (6) the dyestuff 4-nitro- (or 4 : 6-dinitro-) 2-aminophenol --> 1 : 3-dihydroxynaphthalene is coupled with diazotized 4-nitro-2-aminophenol-6-sulphonic acid, and the product is treated with copper (or nickel) sulphate and ferric chloride; (7) the iron compound of the dyestuff 6-nitro-2-aminophenol-4-sulphonic acid --> 1 : 3-dihydroxynaphthalene is coupled with diazotized 4 : 6 dinitro-2-aminophenol, and the product is heated with a solution of ferric chloride, tartaric acid and caustic soda; (8) a mixture of 4-nitro-and 4-chloro-2-aminophenol-6-sulphonic acid is diazotized and coupled with 1 : 3-dihydroxynaphthalene, and the product is heated with a solution of ferric chloride and sodium acetate; part, e.g. half, of the iron may be replaced by copper; (9) 1 : 3-dihydroxynaphthalene is coupled with 6 - nitro - 1 - diazonaphthol - 4 - sulphonic acid and with diazotized 4-chloro-2-aminophenol, 4 - chlor- or 4 - nitro - 2 - aminophenol-6-sulphonic acid, sulphoanthranilic acid (made by sulphonating anthranilic acid) or 6-nitro-1-aminonaphthol-4-sulphonic acid, and the product is heated with a solution of basic chromium sulphate; the chromium may be partly or wholly replaced by iron. Other diazo components specified are metanilic acid, 4-methyl - 2 - aminophenol - 5 - and 6 - sulphonic acids, 6 - chloro - 2 - aminophenol - 4 - sulphonic acid, 2-aminophenol-6-carboxylic-4-sulphonic acid, 4-nitro-2-aminobenzoic acid, 3 : 6-dichloroaminophenol - 4 - sulphonic acid and 1 : 2 : 4-aminonaphtholsulphonic acid. Specification 445,378 is referred to.
GB20046/46A 1942-09-02 1943-08-25 Manufacture of disazo-dyestuffs Expired GB587348A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH587348X 1942-09-02

Publications (1)

Publication Number Publication Date
GB587348A true GB587348A (en) 1947-04-22

Family

ID=4521887

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20046/46A Expired GB587348A (en) 1942-09-02 1943-08-25 Manufacture of disazo-dyestuffs

Country Status (1)

Country Link
GB (1) GB587348A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3017396A (en) * 1958-04-29 1962-01-16 Borden Co Copolymers of vinyl chloride and alkoxyalkyl esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3017396A (en) * 1958-04-29 1962-01-16 Borden Co Copolymers of vinyl chloride and alkoxyalkyl esters

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