GB440150A - Manufacture of dyestuffs containing metal in complex union - Google Patents

Manufacture of dyestuffs containing metal in complex union

Info

Publication number
GB440150A
GB440150A GB7321/35A GB732135A GB440150A GB 440150 A GB440150 A GB 440150A GB 7321/35 A GB7321/35 A GB 7321/35A GB 732135 A GB732135 A GB 732135A GB 440150 A GB440150 A GB 440150A
Authority
GB
United Kingdom
Prior art keywords
aminophenol
dyestuff
nitro
diaminobenzene
sulphonic 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
GB7321/35A
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
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB440150A publication Critical patent/GB440150A/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
    • C09B33/06Disazo dyes in which the coupling component is a diamine or polyamine

Landscapes

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

Abstract

Azo dyestuffs containing metal in complex union are manufactured by the action of an agent yielding metal, e.g. chromium, copper, iron, aluminium, cobalt, nickel, manganese, zinc, vanadium or titanium, on a disazo-dyestuff constructed according to the scheme R --> R1 \sM R where both R's are diazo-components of which at least one contains a metal complex forming group and R1 is an aryl derivative containing at least two amino-groups and capable of coupling twice. The disazo-dyestuffs may be prepared by coupling two similar or different diazo-compounds, at least one of which contains a metal complex forming group, e.g. those of amines of the benzene or naphthalene series which may contain, in o-position to the diazo-group, hydroxy, carboxyl, alkoxy or the salicylic acid grouping, e.g. those of aniline, naphthylamines, o-aminophenol, o-aminonaphthol, o-aminoalkoxybenzene, o-aminoalkoxynaphthalene, anthranilic acids, o-aminonaphthalenecarboxylic acids, aminosalicylic acids, and the sulpho-, nitro-, alkyl- and halogen-substitution products thereof, with an aryleneamine capable of coupling twice, e.g. a phenylene- or naphthylene-diamine, e.g. 1 : 3-phenylenediamine, its 4-sulphonic acid, 1 : 3-diamino - 4 - methylbenzene, 1 : 3 - naphthylenediamine and their nitro-, alkoxy- and halogen-substitution products. The treatment with an agent yielding metal may be effected in acid, neutral or alkaline medium, with or without a suitable addition such as a salt of an inorganic or organic acid or a free organic acid, in the presence or absence of an organic solvent, e.g. alcohol or pyridine, and in an open vessel or under pressure, and may occur simultaneously with the production of the dyestuff, or in substance, on the fibre or in the dye-bath. One agent yielding metal, or several such agents, simultaneously or successively, may be caused to act on a single dyestuff or mixture of dyestuffs, and one atom or more or less than one atom of metal may be introduced for each metal complex forming group in the dyestuff. Dyestuffs containing less than one atom of metal may be made by causing a metal compound of a dyestuff to act on a dyestuff not containing metal, and the product may be treated further with an agent yielding metal. In a modification of the process, a monoazo-dyestuff R --> R1 containing a metal complex forming group or a mixture of such dyestuffs is treated with an agent yielding metal or mixture of such agents and the product is coupled with a second diazo-compound. The products may be further treated with an agent yielding metal or mixture of such agents especially if the second diazo-compound also contains a metal complex forming group. The complex metal compounds may be used for dyeing animal fibres, e.g. wool or silk, or leather tanned in any manner, e.g. chrome or vegetable tanned. In examples: (1) the dyestuff 4-nitro-2-aminophenol --> 1 : 3-diaminobenzene \sM 4 - nitro - 2 - aminophenol-6-sulphonic acid is prepared and is treated with ferric chloride; the product dyes chrome leather olive-brown tints; (2) the dyestuff 4 - nitro - 2 - aminophenol - 5 - sulphonic acid --> 1 : 3 - diaminobenzene \sM 4 - chloro - 2 - amino - phenol is prepared and treated with ferric chloride and copper sulphate; the product dyes chrome leather reddish-dark-brown tints; (3) the dyestuff 6-nitro-2-aminophenol-4-sulphonic acid --> 1 : 3-diaminobenzene is treated with ferric chloride and the product is coupled with diazotized 4-nitro-2-aminophenol and further treated with ferric chloride; the product dyes chrome leather blackish violet-brown tints; (4) the dyestuff 4-chloro-2-aminophenol --> 1 : 3-diaminobenzene \sM 4 - nitro - 2 - aminophenol - 6 - sulphonic acid is prepared in the presence of ferric hydroxide and nickel hydroxide; the product dyes vegetable and chrome tanned leather dark brown tints; (5) the manganous compound of the dyestuff 4-chloro-2-aminophenol-6-sulphonic acid --> 1 : 3-diaminobenzene is coupled with diazotized 2-aminophenol-4-sulphamide and the product is treated with chromium fluoride; the product dyes chrome leather violet brown tints; (6) the cobalt compound of the dyestuff 4-chloro-2-aminophenol-6-sulphonic acid --> 1 : 3-diaminobenzene is coupled with diazotized 2-aminobenzene-1-carboxylic acid and the product is treated with aluminium acetate; the product dyes leather blackish violet-brown tints; (7) the nickel compound of the dyestuff 4-chloro-2-aminophenol-6-sulphonic acid --> 1 : 3-diaminobenzene is coupled with diazotized 4-acetylamino - 1 - aminobenzene; the product dyes chrome leather reddish-brown tints; (8) the dyestuff 6-nitro-2-aminophenol-4-sulphonic acid --> 1 : 3-diaminobenzene \sM 5-amino-2-oxybenzoic acid is prepared and is treated with ferric chloride; the product dyes leather brown tints; (9) the dyestuff 4-nitro-2-aminophenol --> 1-methyl-2 : 4-diaminobenzene \sM 4 - nitro - 2 - aminophenol - 6 - sulphonic acid is prepared in the presence of ferric hydroxide and copper hydroxide; the product dyes chrome leather dark brown tints; (10) the dyestuff 4 : 6-dinitro-2-aminophenol --> 1 : 3-diaminobenzene-4-sulphonic acid \sM 1-amino-8 - oxynaphthalene - 3 : 6 - disulphonic acid is prepared and is treated with cobaltous sulphate; the product dyes chrome leather dark beige to brown tints; (11) 1 : 3-diaminobenzene is coupled with 6-nitro-1-diazo-2-oxynaphthalene-4-sulphonic acid and then with diazotized 6-nitro-2-aminophenol-4-sulphonic acid and the product is treated with ferric chloride and nickel sulphate; the product dyes leather blackish copper-brown tints; (12) the dyestuff 4 - nitro - 2 - aminophenol --> 1 : 3 - diaminobenzene \sM 4-nitro-2-aminophenol-6-sulphonic acid is prepared in the presence of ferric hydroxide and nickel hydroxide; the product dyes leather olive dark-brown tints; (13) the dyestuff 4-nitro-2-aminophenol-6-sulphonic acid --> 1 : 3-diaminobenzene \sM 4 : 6-dinitro-2-aminophenol is treated with chromium fluoride; the product dyes chrome leather violet brown tints; (14) neutralized chrome leather (box calf, chrome sides, glazed kid, full chrome sheep) is dyed an olive dark-brown tint with the iron-nickel compound of the dyestuff 4 - nitro - 2 - aminophenol --> 1 : 3 - diaminobenzene \sM 4 - nitro - 2 - aminophenol - 6-sulphonic acid; (15) vegetable-tanned sheep, goat or calf leather is similarly dyed. A table gives the shades obtained on chrome leather with further metal - containing dyestuffs, additional diazo-components specified being 4-sulpho-2-aminobenzoic acid and 1 : 5-naphthylaminesulphonic acid.
GB7321/35A 1935-01-24 1935-03-08 Manufacture of dyestuffs containing metal in complex union Expired GB440150A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH440150X 1935-01-24

Publications (1)

Publication Number Publication Date
GB440150A true GB440150A (en) 1935-12-20

Family

ID=4515174

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7321/35A Expired GB440150A (en) 1935-01-24 1935-03-08 Manufacture of dyestuffs containing metal in complex union

Country Status (1)

Country Link
GB (1) GB440150A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0091020A1 (en) * 1982-04-02 1983-10-12 BASF Aktiengesellschaft Disazo dyestuffs
EP0191126A1 (en) * 1983-08-09 1986-08-20 BASF Aktiengesellschaft Azo compounds

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0091020A1 (en) * 1982-04-02 1983-10-12 BASF Aktiengesellschaft Disazo dyestuffs
JPS58180558A (en) * 1982-04-02 1983-10-22 バスフ アクチエンゲゼルシヤフト Disazo dye and trisazo dye
US4547566A (en) * 1982-04-02 1985-10-15 Basf Aktiengesellschaft Copper, cobalt, nickel and iron complexes of disazo dyes
US4638055A (en) * 1982-04-02 1987-01-20 Basf Aktiengesellschaft Iron, copper and chromium complexes of disazo dyes
JPH041030B2 (en) * 1982-04-02 1992-01-09 Basf Ag
EP0191126A1 (en) * 1983-08-09 1986-08-20 BASF Aktiengesellschaft Azo compounds

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