GB422605A - Manufacture of chromiferous azo-dyestuffs - Google Patents

Manufacture of chromiferous azo-dyestuffs

Info

Publication number
GB422605A
GB422605A GB9841/34A GB984134A GB422605A GB 422605 A GB422605 A GB 422605A GB 9841/34 A GB9841/34 A GB 9841/34A GB 984134 A GB984134 A GB 984134A GB 422605 A GB422605 A GB 422605A
Authority
GB
United Kingdom
Prior art keywords
naphthol
acid
amino
sulphonic acid
dye
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
GB9841/34A
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 GB422605A publication Critical patent/GB422605A/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
    • C09B45/48Preparation from other complex metal compounds of azo dyes

Landscapes

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

Abstract

Chromiferous azo dyes are made by treating in acid medium a mixture of one or more chromium compounds of azo dyes and one or more chromable azo dyes, the mixture containing at least one chromium compound of an azo dye of the general formula <FORM:0422605/IV/1> wherein the OH and the azo group are in o-position, R=a naphthol residue and the ring X of the naphthalene residue is unsubstituted, as well as at least one azo dye of the said general formula. In examples (1) the dye 1-amino-2-naphthol-4-sulphonic acid --> b - naphthol is treated with chromium formate, the chromium compound is suspended in water with the dye 1-amino-2-naphthol-4-sulphonic acid --> b -naphthol and the mixture refluxed with acetic acid, (2) the chromium compound made in alkaline medium from the dye 1-amino-2-naphthol-4-sulphonic acid --> a -naphthol is heated with the unchromed azo-dye in presence of sulphuric acid, (3) the chromium compound of the dye 1-amino-2-naphthol-4-sulphonic acid --> a -naphthol is heated in acetic acid with the unchromed dye; (4) the mixed chromium compound obtained by treating with chromium formate equal parts of the dyestuffs 1-amino-2-naphthol-4-sulphonic acid --> a -naphthol and 1-amino-2-naphthol-4-sulphonic acid --> b -naphthol are refluxed with the same unchromed azo dyes in presence of formic acid. Examples of the dyeing process are also given. Navy blue to black shades are obtained. The mixtures may contain mono-, dis- and polyazo dyes in which the coupling components may be amines, phenols, pyrazolones, oxyquinolines, barbituric acids, acetoacetic acid and benzoylacetic-o-carboxylic acid and derivatives thereof. The acid medium may be hydrochloric, sulphuric, formic, acetic, oxalic, propionic, benzene sulphonic, a naphthalene disulphonic acid, lactic, or tartaric acid with or without an organic solvent, e.g. alcohol. The treatment may occur in the dye-bath. Specifications 364,148, 384,767, and 408,497 are referred to. The Specification as open to inspection under Sect. 91 comprises also the following examples; (1) the chromium compound produced in alkaline medium from the dye 1-amino-2-naphthol-4-sulphonic acid --> b -naphthol is heated with the unchromed dyestuff in presence of benzene sulphonic acid or tartaric acid; (2) the chromium compound obtained in alkaline medium from the azo dye 1-amino-2-naphthol-4-sulphonic acid --> b -naphthol is refluxed with the azo dyes 1-amino-2-naphthol-4-sulphonic acid --> a -naphthol and 4-nitro 2-aminophenol-6-sulphonic acid --> acetic acid anilide in presence of tartaric acid; (3) the mixed complex chromium compound made in acid medium from the dyes 1-amino-2-naphthol-4-sulphonic acid --> b -naphthol and nitrated 1-diazo-2-naphthol-4-sulphonic acid coupled with b -naphthol is refluxed with the dyestuff 1-amino-2-naphthol-4-sulphonic acid --> a -naphthol in presence of benzene sulphonic acid; (4) the mixed chromium compound of (3) is suspended in aqueous propionic acid and refluxed with the dyes 1-amino-2-naphthol-4-sulphonic acid --> b -naphthol and 1-amino-2-naphthol-4-sulphonic acid --> 1-phenyl-3-methyl-5-pyrazolone; (5) the mixed chromium compound of (3) made with chromium formate is refluxed with the dyestuffs 1-amino-2-naphthol-4-sulphonic acid --> a -naphthol and 2-amino-1-phenol-4-methyl-5-sulphonic acid --> b -naphthol in presence of formic acid; (6) the chromium compound made in acid medium from the dyestuff 1-amino-2-naphthol-4-sulphonic acid --> b -naphthol is refluxed in presence of sulphuric acid with the dyestuffs 2 - amino - 1 - naphthol - 4 - sulphonic acid --> b -naphthol and 2-amino-4-sulphone-benzene carboxylic acid --> p 1-(2<1> methyl-4<1>-sulpho)-phenyl-3-methyl-5-pyrazolone. A table is also given of similar dyestuffs in which the following additional dyestuffs are mentioned as starting materials: 4-chloro-2-aminophenol --> 1 : 5-dioxynaphthalene, 1 - amino - 2 - naphthol - 6-o -sulphomethylamino - 6 - sulphonic acid --> b -naphthol, 4-chlor-2-aminophenol --> chromotropic acid, 4-sulpho-2-amino-1-benzoic acid --> 1-phenyl-3-methyl-5-pyrazolone, 4-chloro-2-aminophenol-5-sulphonic acid -->b -naphthol and 6-nitro-2-amino-1-naphthol-4-sulphonic acid --> a -naphthol. This subject-matter does not appear in the Specification as accepted. Reference has been directed by the Comptroller to Specification 297,331, [Class 2 (iii)].
GB9841/34A 1933-03-31 1934-03-29 Manufacture of chromiferous azo-dyestuffs Expired GB422605A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH422605X 1933-03-31

Publications (1)

Publication Number Publication Date
GB422605A true GB422605A (en) 1935-01-15

Family

ID=4514742

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9841/34A Expired GB422605A (en) 1933-03-31 1934-03-29 Manufacture of chromiferous azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB422605A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3305539A (en) * 1963-12-04 1967-02-21 Crompton & Knowles Corp 1: 1 chromium complex of 2-hydroxynaphthaleneazo-2-hydroxy-6-nitro-7-naphthalene sulfnic acid solubilized with aliphatic carboxylic acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3305539A (en) * 1963-12-04 1967-02-21 Crompton & Knowles Corp 1: 1 chromium complex of 2-hydroxynaphthaleneazo-2-hydroxy-6-nitro-7-naphthalene sulfnic acid solubilized with aliphatic carboxylic acids

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