GB493883A - Manufacture of complex metal compounds of mordant azo-dyestuffs - Google Patents

Manufacture of complex metal compounds of mordant azo-dyestuffs

Info

Publication number
GB493883A
GB493883A GB11265/37A GB1126537A GB493883A GB 493883 A GB493883 A GB 493883A GB 11265/37 A GB11265/37 A GB 11265/37A GB 1126537 A GB1126537 A GB 1126537A GB 493883 A GB493883 A GB 493883A
Authority
GB
United Kingdom
Prior art keywords
acid
chromium
hydroxy
product
amino
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
GB11265/37A
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.)
Durand and Huguenin AG
Original Assignee
Durand and Huguenin 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 Durand and Huguenin AG filed Critical Durand and Huguenin AG
Publication of GB493883A publication Critical patent/GB493883A/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
    • C09B45/00Complex metal compounds of azo dyes
    • C09B45/02Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14Monoazo compounds
    • C09B45/16Monoazo compounds containing chromium

Landscapes

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

Abstract

Complex metal compounds of mordant o-hydroxymonoazo dyestuffs are manufactured by coupling a diazo-compound of an o-aminophenol or a substitution product thereof, particularly a sulphonated derivative, in an alkaline medium with a 1 : 8-aminonaphtholsulphonic acid, in which one hydrogen atom of the amino group is substituted by an -SO2-aryl-o-hydroxycarboxylic acid residue and the other is unsubstituted, particularly a condensation product of 1 : 8-aminonaphtholsulphonic acid with a salicylic acid sulphochloride, and treating the resulting monoazo dyestuff with at least one agent yielding metal, e.g. an agent yielding a bivalent or trivalent metal such as iron or chromium, e.g. by the process described in Specification 26460/12. The products, which may be completely or partially metallized and may also contain several different metals simultaneously, are suitable for application by the customary methods of dyeing and printing with mordant dyestuffs, e.g. by the processes described in Specifications 26460/12, 318,469, 319,457, [all in Class 15 (ii)], and 435,701, to various fibres, e.g. cotton, regenerated cellulose artificial silk or natural silk. In examples: (1) 1-hydroxy - 2 - amino - 4 - chlorobenzene - 6 sulphonic acid is diazotized and coupled with the condensation product from 1-hydroxy-2-carboxybenzene-4-sulphochloride and 1 : 8 : 3 : 6-acid, and the product is treated with a substance yielding chromium, e.g. chromium lactate; silk is dyed with the product in combination with a chromium mordant from an acid bath blue shades; by treating the original dyestuff with copper sulphate, there is obtained the copper compound, which is suitable for chrome printing on cotton, preferably with addition of urea, yielding violet shades; violet shades are also obtained on viscose artificial silk or natural silk by printing with the dyestuff, chromium lactate and tragacanth or gum thickening and steaming; the copper compound, or the corresponding nickel compound, may be further treated with a chromium salt; (2) the sodium salt of picramic acid is diazotized and coupled with the coupling component of (1), and the product is treated with a substance yielding chromium, e.g. chromium acetate; the product can be printed on cotton with chromium acetate, yielding greenish grey prints; (3) 1-amino-2-hydroxy-3-nitro-5-chlorobenzene is diazotized and coupled with the coupling component of (1), and the product is treated with a substance yielding chromium or with a copper salt; the products dye silk with the aid of a chromium mordant greenish blue and violet shades respectively; the copper compound is also suitable for chrome printing on cotton; (4) 1-hydroxy-2-amino - 6 - carboxybenzene - 4 - sulphonic acid is diazotized and coupled with the coupling component of (1), and the product is treated with a compound yielding copper; the product yields reddish violet prints on cotton with the aid of chromium acetate; (5) 5-nitro-3-amino - 4 - hydroxy - 1 - methylbenzene is diazotized and coupled with the coupling component of (1), and the product is converted into its chromium compound, which yields grey-blue shades in chrome printing on cotton; (6) 1 - hydroxy - 2 - amino - 4 - chlorobenzene-6-sulphonic acid is diazotized and coupled with the condensation product from 1-hydroxy-2 - carboxybenzene - 4 - sulphochloride and 1 : 8 : 4 : 6-acid, and the product is converted into its copper compound, which yields red violet prints on cotton with the aid of chromium acetate. Samples have been furnished under Sect. 2 (5) of the chromium and copper compounds of the following dyestuffs; 1 - hydroxy - 2-amino - 4 - chlorobenzene - 6 - sulphonic acid --> the condensation product from 1-hydroxy2 - carboxybenzene - 4 - sulphochloride and 1 : 8 : 4-acid; 1 - hydroxy - 2 - amino - 4-nitrobenzene-6-sulphonic acid --> the same coupling component; 1 - hydroxy - 2 - amino-4 - chlorobenzene - 6 - sulphonic acid --> the condensation product from 1-hydroxy-2-carboxybenzene-4-sulphonic acid and 1 - 8 : 6-acid. The Specification as open to inspection under Sect. 91 comprises also the manufacture of the dyestuffs free from metal. It contains additional examples describing the preparation of the following dyestuffs and their chromium and copper compounds: (a) 5-nitro-3-amino-2 - hydroxy - 1 - methylbenzene --> the condensation product from salicylic acid sulphochloride and 1 : 8 : 3 : 6-acid; (b) 4-nitro-6 - chloro - 2 - aminophenol --> the same coupling component. Reference is made in a table to the dyestuffs obtained by coupling this condensation product with the diazo compounds of p-chloro-o-aminosalicylic acid, 4-chloro - 2 - aminophenol, 5 - nitro - 2 - aminophenol, 5 - nitro - 4 - chloro - 2 - aminophenol and 4 - nitro - 2 - aminophenol - 6 - sulphonic acid. The coupling components of the examples may be replaced by the condensation product of salicylic acid sulphochloride with 1 : 8 : 4-acid. All the metal-free dyestuffs of the examples are described as suitable for chrome printing on cotton, and those of examples (1) and (4) above for dyeing silk with the aid of a chromium mordant. This subject-matter does not appear in the Specification as accepted.
GB11265/37A 1936-04-20 1937-04-20 Manufacture of complex metal compounds of mordant azo-dyestuffs Expired GB493883A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE493883X 1936-04-20

Publications (1)

Publication Number Publication Date
GB493883A true GB493883A (en) 1938-10-17

Family

ID=6544638

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11265/37A Expired GB493883A (en) 1936-04-20 1937-04-20 Manufacture of complex metal compounds of mordant azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB493883A (en)

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