GB573025A - Manufacture of trisazo dyestuffs - Google Patents

Manufacture of trisazo dyestuffs

Info

Publication number
GB573025A
GB573025A GB11658/42A GB1165842A GB573025A GB 573025 A GB573025 A GB 573025A GB 11658/42 A GB11658/42 A GB 11658/42A GB 1165842 A GB1165842 A GB 1165842A GB 573025 A GB573025 A GB 573025A
Authority
GB
United Kingdom
Prior art keywords
methyl
methoxy
amino
diazotised
azobenzene
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
GB11658/42A
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 GB573025A publication Critical patent/GB573025A/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
    • C09B31/16Trisazo dyes

Landscapes

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

Abstract

Trisazo dyes are obtained by coupling, in an alkaline medium, a diazotised aminoazo compound of the general formula R1-N = N-R2-NH2, wherein R1 and R2 represent residues of the benzene series, free from hydroxy, sulphonic or carboxylic acid groups, and in which the azo and amino groups are in m- or p-position to each other on the residue R2, with an aminonaphtholsulphonic acid of the general formula <FORM:0573025/IV/1> wherein one Z represents a primary amino group and the other Z's each represent H, diazotising the resulting disazo compound and coupling with resorcinol or m-aminophenol (1 mol.). The products have affinity for natural or regenerated cellulose fibres and the shade and fastness to wet treatments of the resulting dyeings may be improved by an after-treatment with formaldehyde or with a diazotised aromatic amine. Specified aminoazo compounds are 4-aminoazobenzene and its 3-and 41-methyl, 2 : 21 and 2 : 5-dimethyl, 3-methoxy, 2 - methyl - 5 - methoxy or ethoxy, 2 : 41-dimethyl-5-methoxy, 2 : 5-dimethoxy or diethoxy, 2 - methyl - 21 - or 41 - methoxy and 2-methyl-5 : 41-dimethoxy derivatives, 3-amino-41 - methoxy - azobenzene, 4 - acetylamino - 41 - aminoazobenzene and its 21-methyl, 21-methyl-51 - methoxy, 2 : 21 - dimethyl - 51 - methoxy, 2 - chloro-21-methyl-51-methoxy and 2 : 6-dichloro-21-methyl - 51 - methoxy derivatives, 3 - acetyl - amino - 21 - methyl - 51 - methoxy - 41 - aminoazo - benzene, 4 - formylamino - 21 - methyl - 41 - amino - azobenzene, 4-aminoazobenzene-41-oxamic acid and its 2-methyl and 2-methyl-5-methoxy derivatives, 4 - nitro - 41 - aminoazobenzene and its 2-, 21- and 31 - methyl, 21 : 51 - dimethyl, 21 - methyl - 51 - methoxy, 2- and 31 - methoxy, 21 : 51 - dimethoxy and 2 - chloro derivatives, 5-nitro-2-methyl-41-aminoazobenzene, 3-nitro-21 - methyl - 51 - methoxy - 41 - aminoazobenzen and 4 - amino - 2 - methyl - azobenzene - 31 - oxamic acid and its 5-methoxy derivative. Specified aminonaphtholsulphonic acids are the 1 : 5 : 7-, 2 : 5 : 7- and 2 : 8 : 6-acids. Examples relate to the production of the dyestuffs, (1) 4-amino-3-methoxy-azobenzene --> (alkaline) 2 : 8 : 6-acid --> resorcinol, which dyes cotton brown violet, becoming a readily dischargeable olive brown, fast to washing, on development with diazotised 4-nitroaniline; (2) 4-amino-2-methyl-5-methoxy-azobenzene --> (alkaline) 1 : 5 : 7-acid --> resorcinol, which dyes cotton grey-violet, becoming a readily dischargeable olive brown, fast to washing, on development with diazotised 4-nitroaniline; (3) 4-amino-2-methyl-41-methoxy-azobenzene --> (alkaline) 2 : 8 : 6-acid --> 3-aminophenol, which dyes cotton violet brown, becoming a readily-dischargeable brown, fast to washing, on development with diazotised 4-nitroaniline; (4) 4-acetylaminoaniline --> 3-toluidine --> (alkaline) 2 : 8 : 6-acid --> resorcinol, which dyes cotton violet brown, becoming fast to washing on after-treatment with formaldehyde and becoming a dischargeable brown, fast to washing, on development with diazotised 4-nitroaniline; if the 3-toluidine is replaced by cresidine, the product dyes cotton grey green, becoming fast to washing on after-treatment with formaldehyde and becoming a dischargeable olive black, fast to washing, on development with diazotised 4-nitroaniline. A table is given showing the shades obtainable on cotton on development with diazotised 4-nitroaniline of the dyeings with the dyestuffs from various combinations of components. Examples are also given of the dyeing process as applied to cotton with (a) development with diazotised 4-nitroaniline, (b) after-treatment with formaldehyde. The Specification as open to inspection under Sect. 91 comprises also the use as amino-azo compound of 4-amino-41-hydroxy-21-methyl-azobenzene. This subject - matter does not appear in the Specification as accepted. 3 - Amino - 41 - methoxy - azobenzene is obtained by reducing the nitro group in the product obtained by methylating the dyestuff, 3-nitroaniline --> phenol.
GB11658/42A 1941-09-02 1942-08-19 Manufacture of trisazo dyestuffs Expired GB573025A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH573025X 1941-09-02

Publications (1)

Publication Number Publication Date
GB573025A true GB573025A (en) 1945-11-02

Family

ID=4521031

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11658/42A Expired GB573025A (en) 1941-09-02 1942-08-19 Manufacture of trisazo dyestuffs

Country Status (1)

Country Link
GB (1) GB573025A (en)

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