GB758087A - New disazo-dyestuffs and process for making them - Google Patents

New disazo-dyestuffs and process for making them

Info

Publication number
GB758087A
GB758087A GB9710/53A GB971053A GB758087A GB 758087 A GB758087 A GB 758087A GB 9710/53 A GB9710/53 A GB 9710/53A GB 971053 A GB971053 A GB 971053A GB 758087 A GB758087 A GB 758087A
Authority
GB
United Kingdom
Prior art keywords
acid
aryl
coupling
groups
ester
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
GB9710/53A
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 GB758087A publication Critical patent/GB758087A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C09B43/24—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with formation of —O—SO2—R or —O—SO3H radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24—Disazo or polyazo compounds

Landscapes

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

Abstract

3 : 31-Dihydroxybenzidine is converted into its disulphuric ester by means of chlorsulphonic acid in an inert organic dispersing medium. The product forms alkali salts. An example is given of the production of the di-sodium salt.ALSO:The invention comprises disazo dyestuffs of the formula <FORM:0758087/IV(c)/1> where X is a cation and the aryl radicals are the same or different. These are made from 3:31-dioxybenzidine by (1) converting the hydroxyl groups into sulphuric ester groups, and (2) diazotizing and coupling with two mols of the same or different N-aryl-J acid, the two operations being performed in either order. Preferably the aryl groups are benzene residues free from solubilizing groups but optionally carrying other substituents such as methyl, methoxyl or chlorine. For tetrazotizing the benzidine disulphuric ester it is preferably converted into its alkali salt and tetrazotized in the presence of a carboxylic acid such as acetic or benzoic. Coupling with the N-aryl-J acid may take place in the presence of an alkaline earth hydroxide, alcohols, acetone, pyridine, picolines or ethanolamines. Esterification after coupling is effected with chlorsulphonic acid in a tertiary base, The products are suitable for dyeing or printing wool, silk, leather, linen, cotton, regenerated cellulose, superpolyamides and superpolyurethanes. They may be metallized in substance, in the dyebath or on the fibre, e.g. by the process of Specification 455,274 [Group IV] or 619,969. Specified metals are iron, manganese, chromium, cobalt, nickel or copper. Examples show the production of the disazo dyestuff from N-phenyl-J acid with esterification before and after coupling. A further example describes the dyeing of cotton with the product and after-coppering; a blue shade is obtained. Other specified N-aryl groups are o-tolyl, p-tolyl, p-chlorophenyl and p-methoxyphenyl.
GB9710/53A 1952-04-10 1953-04-09 New disazo-dyestuffs and process for making them Expired GB758087A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH758087X 1952-04-10

Publications (1)

Publication Number Publication Date
GB758087A true GB758087A (en) 1956-09-26

Family

ID=4534454

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9710/53A Expired GB758087A (en) 1952-04-10 1953-04-09 New disazo-dyestuffs and process for making them

Country Status (4)

Country Link
BE (1) BE519082A (en)
DE (1) DE943369C (en)
GB (1) GB758087A (en)
NL (2) NL83316C (en)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR487778A (en) * 1917-01-23 1918-07-24 Soc Ind Chimique Bale Process for the preparation of new copper combinations of substantive azo dyes
US1775605A (en) * 1926-12-13 1930-09-09 Gen Aniline Works Inc New azo dyestuffs
DE538108C (en) * 1926-12-14 1931-11-11 I G Farbenindustrie Akt Ges Process for the preparation of azo dye derivatives
DE684524C (en) * 1936-02-21 1939-11-30 I G Farbenindustrie Akt Ges Process for the preparation of disazo dyes
BE453075A (en) * 1941-02-18

Also Published As

Publication number Publication date
NL83316C (en)
DE943369C (en) 1956-05-17
BE519082A (en)
NL177467B (en)

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