GB347742A - Manufacture of disazo-dyestuffs - Google Patents

Manufacture of disazo-dyestuffs

Info

Publication number
GB347742A
GB347742A GB3216/30A GB321630A GB347742A GB 347742 A GB347742 A GB 347742A GB 3216/30 A GB3216/30 A GB 3216/30A GB 321630 A GB321630 A GB 321630A GB 347742 A GB347742 A GB 347742A
Authority
GB
United Kingdom
Prior art keywords
acid
amino
sulphonic
alkaline
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
GB3216/30A
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 GB347742A publication Critical patent/GB347742A/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
    • C09B31/00Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02Disazo dyes
    • C09B31/08Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups

Landscapes

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

Abstract

Disazo dyes; regenerated celluloses, dyeing.-Secondary disazo dyes dyeing blue tints are obtained by coupling a diazo compound which does not carry hydroxyl in o- or p-position to the diazo group with a sulphonated or unsulphonated ether of 1 : 2-aminonaphthol, rediazotizing, and coupling (alkaline) with a 2 : 5 : 7-aminonaphtholsulphonic acid or an N-aryl derivative thereof containing no external amino group, the product, if necessary, being saponified. The dyeings on cotton and regenerated cellulose fibres, ranging from violet-blue to green-blue, are fast to light, and some of them give level dyeings on "stripey" viscose. They are convertible into dyestuffs containing metal by treatment with an agent yielding metal applied either to the disazo product or during the final coupling or applied in the dyebath or on the fibre. The following examples are specified: (1) The dyestuff aniline-2-sulphonic acid --> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> (alkaline) phenyl-2 : 5 : 7-acid dyes regenerated cellulose silk level clear blue shades. (2) The dyestuff 2-aminonaphthalene-4 : 8-disulphonic acid --> 1-amino-2-ethoxynaphthalene --> (in aqueous pyridine solution) 2 : 5 : 7-acid dyes regenerated silk level blue shades; there may also be used as first components sulphanilic acid, metanilic acid, 4-aminoacetanilide, 4-aminoacetanilide-3-sulphonic acid, 4-chloraniline-2-sulphonic acid, 2-acetylamino-4-chloro-5-aminophenol methyl ether, xylidinesulphonic acid (CH3 : CH3 : NH2 : SO3H = 1 : 3 : 4 : 5), chlorotoluidinesulphonic acid (CH3 : NH2 : Cl : SO3H = 1 : 2 : 5 : 3), aniline-2 : 5-disulphonic acid, toluidine-2 : 5-disulphonic acid (CH3 : NH2 : SO3H = 1 : 4 : 2 : 5), 41-methyl-2-aminodiphenylsulphone-4-sulphonic acid, p-amino-salicylic acid, 3 - amino - 4 - sulphobenzoic acid, 41-methyl-4-aminodiphenylamine-2-sulphonic acid, 2 : 6- (or 2 : 7-)naphthylaminesulphonic acid, 2 : 4 : 8-naphthylaminedisulphonic acid, 1 : 5 : 7-aminonaphtholsulphonic acid, or H-acid (preferably as the O-ester); other suitable middle components are 1-amino-2-methoxynaphthalene, and 1-amino2-ethoxynaphthalene-6-(or 7-)sulphonic acid, and homologues thereof; other suitable end components are the various N-tolyl, N-xylyl, N-anisidyl, N-oxyphenyl, and N-oxycarboxyphenyl derivatives of 2 : 5 : 7-acid; specified dyestuffs are the saponified product from 2-acetylamino-4-chloro-5-aminophenol methyl ether --> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> (alkaline) 2 : 5 : 7-acid, 41-methyl-4-aminodiphenylamine-2-sulphonic acid --> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> (alkaline) 2 : 5 : 7-acid, and sulphanilic acid --> 1-amino - 2 - methoxynaphthalene - 6 - sulphonic acid --> (alkaline) phenyl-2 : 5 : 7-acid. (3) The dyestuff metanilic acid --> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> (alkaline) phenyl-2 : 5 : 7-acid is boiled with a solution of copper sulphate or of a cuprammonium salt; the product gives from a feebly alkaline bath blue shades more greenish than those from the uncoppered dyestuff; the coppering may also be effected in the dyebath or on the fibre; the dyestuffs containing o-oxycarboxy groups are particularly suitable for conversion into metal compounds. Examples are also given of the dyeing processes for cotton and for viscose. Specifications 12119/98, 14248/07, [both in Class 2, Acids and salts, Organic &c.], 292,660, and 301,754, [both in Class 2 (iii), Dyes &c.], are referred to. Chlorotoluidinesulphonic acid (CH3 : NH2 : Cl : SO3H = 1 : 2 : 5 : 3) is obtained by baking the sulphate of 5-chloro-2-toluidine. 1-Amino-2-ethoxynaphthalene-7-sulphonic acid is obtained by ethylating 2 : 7-naphtholsulphonic acid, nitrating the product and reducing the nitro group. The Specification as open to inspection under Sect. 91 (3) (a) comprises also (1) the use of any diazotizable first component, (2) the use as end components of sulphonic acids of 2 : 5- and 2 : 8-aminonaphthols and their N-substitution products in general, containing no external amino group, additional specified components being N-acidyl, N-alkyl, and N-aralkyl derivatives of 2 : 5 : 7-acid, and the following acids and their N-acidyl, N-alkyl, N-aralkyl, and N-aryl derivatives, viz. 2 : 8 : 6-acid and 2 : 5 : 1 : 7- and 2 : 8 : 3 : 6-aminonaphtholdisulphonic acids. This subject-matter does not appear in the Specification as accepted.
GB3216/30A 1929-02-02 1930-01-30 Manufacture of disazo-dyestuffs Expired GB347742A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH347742X 1929-02-02

Publications (1)

Publication Number Publication Date
GB347742A true GB347742A (en) 1931-04-30

Family

ID=4508110

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3216/30A Expired GB347742A (en) 1929-02-02 1930-01-30 Manufacture of disazo-dyestuffs

Country Status (1)

Country Link
GB (1) GB347742A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2476260A (en) * 1946-04-11 1949-07-12 Ciba Ltd Process for the manufacture of disazo-dyestuffs
US2476261A (en) * 1946-04-11 1949-07-12 Ciba Ltd Process for the manufacture of asymmetrical polyazo-dyestuffs

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2476260A (en) * 1946-04-11 1949-07-12 Ciba Ltd Process for the manufacture of disazo-dyestuffs
US2476261A (en) * 1946-04-11 1949-07-12 Ciba Ltd Process for the manufacture of asymmetrical polyazo-dyestuffs

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