GB434835A - Manufacture of new chromiferous dyestuffs - Google Patents

Manufacture of new chromiferous dyestuffs

Info

Publication number
GB434835A
GB434835A GB11829/34A GB1182934A GB434835A GB 434835 A GB434835 A GB 434835A GB 11829/34 A GB11829/34 A GB 11829/34A GB 1182934 A GB1182934 A GB 1182934A GB 434835 A GB434835 A GB 434835A
Authority
GB
United Kingdom
Prior art keywords
naphthol
acid
sulphonic acid
aminonaphthol
dyestuffs
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
GB11829/34A
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 GB434835A publication Critical patent/GB434835A/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
    • C09B45/01Complex metal compounds of azo dyes characterised by the method of metallisation

Landscapes

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

Abstract

Azo dyes, chromium compounds of; dye mixtures; acid wool dyes, dyeing with.--Chromiferous dyestuffs are obtained by the action of an alkaline chromium oxide solution on a mixture of chromable monoazo dyes of which at least one is of the general formula <FORM:0434835/IV/1> wherein R1 is a naphthalene residue, R2 is a naphthol residue, n is 1, 2 or 3 and the OH group is in o-position to the azo group, the amount of chromium oxide being sufficient to provide at least one atom of chromium for each chromable group in the dyestuffs. The chroming and the production of the dyestuffs may be effected in a single operation. The chromable mono-azo dyes not of the above general formula may be, for example, those obtainable by coupling a diazotized aromatic amine of the benzene or naphthalene series with an arylamine, phenol, pyrazolone, oxyquinoline, barbituric acid, acetoacetic acid derivative or benzoylaceto-o-carboxylic acid derivative. The chromiferous products are suitable for dyeing animal fibres, e.g. wool and silk, wool being conveniently dyed by the processes of Specifications 364,148 or 408,497. The following examples are specified. (1) A mixture of the dyestuff, 1 : 2-aminonaphthol-4-sulphonic acid --> 2-naphthol, with the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol - 4 - sulphonic acid and 2 - naphthol is stirred into a solution of a freshly precipitated chromium hydroxide paste in 90 per cent caustic potash and the mixture is heated for 10--12 hours at 75--78 DEG C. and for a further 2--3 hours at 80--85 DEG C.; the whole is then diluted, mineral acid is added until the reaction is feebly alkaline and the dyestuff is salted out; alternatively, the 2-naphthol may be dissolved in the chromite solution, the diazotized 1 : 2-aminonaphthol-4-sulphonic acid introduced at 20 DEG C. and the nitrated diazotized 1 : 2 - aminonaphthol - 4 - sulphonic acid at 0--5 DEG C.; the product gives fast navy blue dyeings on wool from an acid bath. (2) 2 - Naphthol is dissolved in a solution of chromium hydroxide in 90 per cent caustic potash, the solution is cooled to 10--15 DEG C., a paste of diazotized 1 : 2-amino-naphthol - 4 - sulphonic acid is added with cooling to 8--10 DEG C. and further addition of a neutral solution of diazotized 4-methyl-2-aminophenol-5-sulphonic acid and the mixture is then heated for 12 hours at 74--78 DEG C. and for a further 4 hours at 80--85 DEG C.; the mixture is then diluted and neutralized and the dyestuff is salted out; the product gives reddish navy blue dyeings on wool from a sulphuric acid bath. (3) Wool is dyed a very fast navy blue by handling it for 10--15 minutes in dilute sulphuric acid at 60 DEG C., adding a solution of the dyestuff of (1), maintaining the bath at 60 DEG C. for 30 minutes, raising gradually to the boil, adding more sulphuric acid and boiling for 30--45 minutes. (4) Wool is dyed a fast dark navy blue by handling it for 10 minutes in dilute formic acid at 85--90 DEG C., adding a solution of the dyestuff of (1), boiling, adding more formic acid, boiling for 20--30 minutes, adding sulphuric acid and boiling for 30 minutes, adding more sulphuric acid gradually and boiling for 75--90 minutes. (5) Wool is dyed a fast reddish navy blue by entering it into a solution at 60--70 DEG C. of the dyestuff of (2) in dilute sulphuric acid with an addition of benzenesulphonic acid or its sodium salt, raising the temperature to the boil during 30 minutes and continuing to boil for 60--75 minutes. (6) Ordinary or loaded silk is dyed a fast reddish navy blue by entering it into a solution at 50--60 DEG C. of the dyestuff of (2) in dilute acetic acid, heating the bath gradually to 80 DEG C. and maintaining this temperature for 45--60 minutes. The samples furnished under Sect. 2 (5) are of chromed dyestuffs from mixtures of (a) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid --> 2-naphthol and 2 : 1-aminonaphthol-4-sulphonic acid --> 2-naphthol; (b) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid --> 2-naphthol and 4-chloro-2-aminophenol --> 1 : 8-dioxynaphthol-3 : 6-disulphonic acid; (c) the dyestuff 1 : 2-aminonaphthol-4-sulphonic acid --> 1-naphthol and the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol-4-sulphonic acid and 2-naphthol; (d) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid --> 1-naphthol and 4-methyl-2-aminophenol --> 2-naphthol; (e) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid --> 2-naphthol and 2-aminophenol-4 : 6-disulphonic acid-->1-phenyl-3-methyl-5-pyrazolone; (f) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid --> 2-naphthol, 4-chloro-2-aminophenol --> resorcinol and 4 - nitro - 2 - aminophenol - 6-sulphonic acid --> 2-naphthol; (g) the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol-4-sulphonic acid --> 2-naphthol and the dyestuffs 2-aminophenol-4-sulphamide --> 1-(3<1>-sulphophenyl)-3-methyl-5-pyrazolone and 4-nitro-2-aminophenol-6-sulphonic acid --> acetoacetanilide; (h) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid and 2-naphthol, 2 - aminophenol - 4 : 6 - disulphonic acid --> 1-phenyl-3-methyl-5-pyrazolone and 4-nitro-2-aminophenol-6-sulphonic acid --> 1-phenyl-3-methyl-5-pyrazolone; (i) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid --> 2-naphthol and 2 : 1-aminonaphthol-4-sulphonic acid --> 2-naphthol, in proportions differing from those in (a) above; (j) the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol-4-sulphonic acid and 2-naphthol and the dyestuffs 4 - nitro - 2 - aminophenol - 6 - sulphonic acid --> acetoacetanilide and 4-nitro-2-aminophenol-6-sulphonic acid --> 1-phenyl-3-methyl-5-pyrazolone; (k) the dyestuff from the nitrated diazo compound of 1 : 2-aminonaphthol-4-sulphonic acid and 2-naphthol, the reduction product of the same and the dyestuff 4-chloro-2-aminophenol-5-sulphonic acid --> barbituric acid; (l) the dyestuffs 1 : 2-aminonaphthol-4-sulphonic acid --> 1-naphthol and 4-methyl-2-aminophenol-5-sulphonic acid --> 2-naphthol. Reference has been directed by the Comptroller to Specification 297,331, [Class 2 (iii)].
GB11829/34A 1933-04-21 1934-04-19 Manufacture of new chromiferous dyestuffs Expired GB434835A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH434835X 1933-04-21

Publications (1)

Publication Number Publication Date
GB434835A true GB434835A (en) 1935-09-10

Family

ID=4515037

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11829/34A Expired GB434835A (en) 1933-04-21 1934-04-19 Manufacture of new chromiferous dyestuffs

Country Status (1)

Country Link
GB (1) GB434835A (en)

Similar Documents

Publication Publication Date Title
US2551056A (en) Chrome monoazo dyestuffs
US2985646A (en) Chromium-containing dyestuffs
US2109552A (en) Azo dyestuffs and their metalliferous derivatives
US2708193A (en) Water-soluble chromium-containing azo dyestuffs
US2683707A (en) Complex chromium compounds of
US2803625A (en) Chromium complex disazo dyestuffs
GB434835A (en) Manufacture of new chromiferous dyestuffs
US2479944A (en) Metallized benzimidazole azo dyestuffs
US2305747A (en) Complex chromium compounds of ortho-hydroxyazo dyestuffs and process of making same
US2405816A (en) O:o&#39;-dihydroxy azo dyestuffs and a process for their manufacture
US2111270A (en) Metalliferous azo dyestuffs and a process for producing same
US2061545A (en) Conversion products of azo dyestuffs and their production
US2452171A (en) Metallizable monoazo dyes
US2248151A (en) Production of substantive azo dyestuffs
EP0027950B1 (en) Fibre-reactive chromium complex dyestuffs, their preparation and their use
US2447867A (en) Azo dyestuffs of the pyrazolone series
US1855289A (en) Manufacture of water soluble azo dyestuffs
US2140944A (en) Azo dyes
US2034304A (en) Azo dyestuffs and their production
US1716098A (en) Trisazo dye and process of producing the same
US2205481A (en) Monoazo dyestuffs
US3492285A (en) Monoazo dyestuffs containing a 4-organoamino - methylene - 1 - hydroxynaphthalene-2-carboxylic acid group
US3116276A (en) Water-insoluble metalliferous azo-dyestuffs and a process for their manufacture
US2412767A (en) Process for preparing mordant triazol dyestuffs
US2328465A (en) Metalliferous substantive dyestuffs