GB601266A - Manufacture of polyazo-dyestuffs - Google Patents

Manufacture of polyazo-dyestuffs

Info

Publication number
GB601266A
GB601266A GB20312/45A GB2031245A GB601266A GB 601266 A GB601266 A GB 601266A GB 20312/45 A GB20312/45 A GB 20312/45A GB 2031245 A GB2031245 A GB 2031245A GB 601266 A GB601266 A GB 601266A
Authority
GB
United Kingdom
Prior art keywords
amino
oxy
group
mol
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
GB20312/45A
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 GB601266A publication Critical patent/GB601266A/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
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/12Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Landscapes

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

Abstract

Polyazo dyestuffs capable of being after-coppered on the fibre and having the general formula <FORM:0601266/IV (c)/1> (in which R1, R2 and R3 represent unsulphonated benzene nuclei, of which R1 contains an oxy-group in ortho-position to the azo group, R2 contains the -NH- and azo groups in 1,4-position relatively to one another, and R3 contains a hydroxyl group in 4-position to the azo group and a carboxyl group in orthoposition to the said hydroxyl group, and R4 represents an unsulphonated benzene nucleus which may, if desired, contain as a substituent in the 4-position relatively to the -NH- group a -N=N-R5 group, in which R5 represents a benzene nucleus free from sulphonic acid groups and containing a hydroxyl group in 4-position relatively to the azo-group and a carboxyl group in ortho-position to the said hydroxyl group) are prepared from 1 mol. of a diazotized ortho-aminophenol free from sulphonic acid groups, 1 mol. of 2-amino-5-oxynaphthalene-7-sulphonic acid, 1 mol. of cyanuric chloride or bromide, and 1 or 2 mols. of a 4-amino-41-oxy-1,11-azobenzene-31-carboxylic acid or 1 mol. each of two such acids, the order of succession of the operations and the conditions being such that the diazo-compound couples in the 6-position of the amino-oxynaphthalene sulphonic acid, one halogen atom of the cyanuric halide reacts with the amino group of the amino-oxynaphthalene sulphonic acid, 1 or 2 halogen atoms of the cyanuric halide react with the amino group or groups of the amino-oxy-azobenzene carboxylic acid or acids and, if an unreacted halogen atom remains, this is reacted with a primary amine of the benzene series free from sulphonic acid groups. In a modified process, the amino-oxy-azobenzene carboxylic acid or acids are replaced by an amine or amines of the benzene series containing an amino group or a group convertible thereto in the 4-position, and the product is diazotized or tetrazotized and coupled with 1 or 2 mols. of an ortho-oxy-benzene carboxylic acid or acids capable of coupling in paraposition to the hydroxyl group, these reactions being carried out after reaction of the cyanuric halide with the 2-amino-5-oxynaphthalene-7-sulphonic acid and the coupling with the diazotized ortho-aminophenol. In a modification, and by similar procedures, dyestuffs of the general formula <FORM:0601266/IV (c)/2> are obtained from 1 mol. of a diazotized orthoaminophenol free from sulphonic acid groups, 1 mol. of 2-amino-5-oxynaphthalene-7-sulphonic acid, 1 mol. of phosgene and 1 mol. of a 4-amino-41-oxy-1,11-azobenzene-31-carboxylic acid. In examples: (1) 1-amino-2-oxybenzene-5-sulphonamide (1-amino-2-oxy-5-nitrobenzene or 1-amino-2-oxy-5-chlorobenzene) is diazotized and coupled in alkaline solution with a condensation product obtained from 1 mol. each of cyanuric chloride, 2-amino-5-oxynaphthalene-7-sulphonic acid, 4 - amino - 41 - oxy - 1,11 - azobenzene-31-carboxylic acid and aniline; (2) 1 - amino - 2 - oxybenzene - 5 - sulphonamide - (1 - amino-2-oxy-5-nitrobenzene or 1-amino-2-oxy-5-chlorobenzene) is diazotized and coupled in alkaline solution with the condensation product obtained from 1 mol. of cyanuric chloride, 1 mol. of 2-amino-5-oxynaphthalene-7-sulphonic acid and 2 mols. of 4-amino-41-oxy-1,11-azobenzene-31-carboxylic acid; and (3) cotton is dyed in a bath containing the dyestuff of example (1) under addition of sodium sulphate and the dyebath is then neutralized and copper sulphate and tartaric acid added. Specifications 209,723, [Class 15 (ii)], 221,843 and 315,665, [both in Class 2 (iii)], are referred to.
GB20312/45A 1944-08-09 1945-08-08 Manufacture of polyazo-dyestuffs Expired GB601266A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH601266X 1944-08-09

Publications (1)

Publication Number Publication Date
GB601266A true GB601266A (en) 1948-05-03

Family

ID=4522766

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20312/45A Expired GB601266A (en) 1944-08-09 1945-08-08 Manufacture of polyazo-dyestuffs

Country Status (1)

Country Link
GB (1) GB601266A (en)

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