GB583043A - Manufacture of monoazo-dyestuffs - Google Patents

Manufacture of monoazo-dyestuffs

Info

Publication number
GB583043A
GB583043A GB21463/43A GB2146343A GB583043A GB 583043 A GB583043 A GB 583043A GB 21463/43 A GB21463/43 A GB 21463/43A GB 2146343 A GB2146343 A GB 2146343A GB 583043 A GB583043 A GB 583043A
Authority
GB
United Kingdom
Prior art keywords
aminophenol
nitro
hydroxy
acid
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
GB21463/43A
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 GB583043A publication Critical patent/GB583043A/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

Abstract

Monoazo dyestuffs are manufactured by coupling diazo-compounds of the benzene series containing a hydroxy group in o-position to the diazo-group with 2 : 6-dihydroxynaphthalenes which have no further substituents in the naphthalene nucleus and in which one hydroxy group is etherified to form an alkoxy (e.g. methoxy or ethoxy) group or a substituted alkoxy group (e.g. one in which the alkyl residue is that of a polyhydric alcohol, such as ethylene glycol or glycerol, or contains a group imparting solubility in water, such as a carboxyl group). The resulting dyestuffs may be treated with an agent yielding metal (e.g. chromium), in substance (e.g. in acid, neutral or alkaline medium, with or without a suitable addition such as an acid, a neutral salt, a base, an acid-binding agent or an inert solvent, and with or without the application of pressure), in the dyebath or on the fibre (e.g. with the addition of a neutral chromlte and an ammonium salt to the dyebath). The products may be used as pigment dyestuffs, or for dyeing or printing a variety of fibres, e.g. vegetable fibres such as cotton, viscose artificial silk and especially animal fibres such as wool, silk and leather; e.g. some of them dye wool by the after-chroming or single bath process in olive, olive-green or grey shades. Examples (1) to (9) describe the preparation of the following dyestuffs: 4- (or 6-) nitro-2-aminophenol-6-(or 4-) sulphonic acid, 4 : 6-dinitro-2-aminophenol, 4 - chloro - 2 - aminophenol - 6 - sulphonic acid or 4-methyl-2-aminophenol-5- or 6-sulphonic acid (or a mixture of the last two compounds) --> 2-hydroxy-6-methoxynaphthalene; 4 : 6-dinitro-, 5-nitro- or 4-chloro-6-nitro-2-aminophenol, or 4-nitro- or 4-chloro-2-aminophenol-6-sulphonic acid --> glycerol a -mono-(6 - hydroxy - 2 - naphthyl) - ether; 5 - nitro- or 4-chloro-6-nitro-2-aminophenol --> 2-hydroxynaphthalene-6-oxyacetic acid. In further examples: (10) the dyestuff 4-chloro-2-aminophenol-6-sulphonic acid --> 2-hydroxy-6-methoxynaphthalene is boiled with an aqueous solution of chromium fluoride; (11) the dyestuff 4-nitro-2-aminophenol-6-sulphonic acid --> 2-hydroxy-6-methoxynaphthalene is similarly chromed and the product is converted into its sodium salt by addition of sodium carbonate; (12) wool is dyed with the dyestuff 4-nitro-2-aminophenol-6-sulphonic acid --> 2-hydroxy-6-methoxynaphthalene from a bath containing acetic acid and Glauber salt and, during the later stages, sulphonic acid, and is after-treated in the same bath with potassium bichromate, yielding an olive shade; (13) wool is dyed grey-green with the product of (11) from a bath containing sulphuric acid. Glycerol-a -mono-(6-hydroxy-2-naphthyl) ether is obtainable by heating 2 : 6-dihydroxynaphthalene with glycerol a -monochlorhydrin in aqueous potassium hydroxide solution. 2-Hydroxynaphthalene-6-oxyacetic acid is obtainable similarly from 2 : 6-dihydroxynaphthalene and potassium chloracetate. The Specification as open to inspection under Sect. 91 comprises the use of any diazo compounds containing lake-forming groups (including those of the naphthalene series) and, as coupling component, any monoether of a dioxynaphthalene in which the hydroxyl groups are in b -position and both o-positions with respect to the free hydroxyl group are unsubstituted. Additional examples describe the production of dyestuffs by coupling 2-hydroxy-6-methoxynaphthalene with 1 - diazo - 2 - naphthol - 4 - sulphonic acid or its 6-nitro derivative, and the conversion of the former of these dyestuffs to its chromium compound by refluxing with chromium fluoride solution. This subject-matter does not appear in the Specification as accepted.
GB21463/43A 1942-12-22 1943-12-22 Manufacture of monoazo-dyestuffs Expired GB583043A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH583043X 1942-12-22

Publications (1)

Publication Number Publication Date
GB583043A true GB583043A (en) 1946-12-05

Family

ID=4521623

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21463/43A Expired GB583043A (en) 1942-12-22 1943-12-22 Manufacture of monoazo-dyestuffs

Country Status (1)

Country Link
GB (1) GB583043A (en)

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