GB682024A - Manufacture of trisazo dyestuffs - Google Patents

Manufacture of trisazo dyestuffs

Info

Publication number
GB682024A
GB682024A GB17976/50A GB1797650A GB682024A GB 682024 A GB682024 A GB 682024A GB 17976/50 A GB17976/50 A GB 17976/50A GB 1797650 A GB1797650 A GB 1797650A GB 682024 A GB682024 A GB 682024A
Authority
GB
United Kingdom
Prior art keywords
resorcinol
amino
acid
coupled
diazotized
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
GB17976/50A
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 GB682024A publication Critical patent/GB682024A/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
    • C09B35/00Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/38Trisazo dyes ot the type
    • C09B35/40Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound

Landscapes

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

Abstract

Substituted anilides of m- and p-aminobenzoic acids are made by (1) condensing a m-or p-nitraniline with m- or p-nitrobenzoyl chloride and reducing the two nitro groups in the product, or (2) condensing a m- or p-phenylene diamine with m- or p-nitrobenzoyl chloride and reducing the nitro group in the product. The nitraniline may contain nuclear substituents, e.g. chlorine or other halogen, methyl or methoxy but not carboxylic acid groups; suitable compounds are listed. The diamine may be similarly substituted, p-phenylene diamine monosulphonic acid being specified. Examples are given of the production of 2 - amino - 5 - (p - aminobenzamido) toluene and 2 : 5 - dimethoxy - 4 - (p - aminobenzamido)-aniline by method (1).ALSO:The invention comprises trisazo dyestuffs of the formula <FORM:0682024/IV (c)/1> where R1, R2, R3 and R4 are benzene residues, the attachments to R2 and R3 being m- or p-; R1 contains a hydroxy group pto the azo linkage and carboxyl group oto the hydroxyl; R4 contains an o-oxy or o-alkoxy group or metallized derivative thereof; R3 is free from carboxylic groups; the azo groups are attached to the nucleus I oto the hydroxy groups. These dyestuffs may be made by coupling resorcinol successively in either order with diazotized R4NH2 and the diazo compound of an amino-azo dyestuff R1-N=N-R2-CO-HN -R3-NH2. Alternatively salicylic acid or a substitution derivative thereof p may be coupled with the diazo compound of an amino-azo dyestuff of the formula <FORM:0682024/IV (c)/2> Metallization may be effected by treating the final dyestuff or a metallizable intermediate thereof with an agent yielding metal, e.g. copper, chromium, nickel or cobalt. Preferably conditions are chosen so that the salicylic acid grouping in R1 is not metallized. Alternatively metallization may be carried out in the dyebath and/or on the fibre, e.g. as in Specifications 455,274 and 619,969. The products are suitable for dyeing or printing animal and cellulosic fibres, e.g. wool, silk, leather, linen, cotton and regenerated cellulose. Substituents that may be present on the benzene nuclei are: R1, chlorine, methyl; R3, chlorine or other halogen, methyl, methoxy, sulphonic acid; R4, sulphonic acid, carboxylic acid or amide, sulphonamide, chlorine. The diazo compounds of R1-N= N-R2-CO-HN-R3-NH2 may be made by tetrazotizing a diamine H2N-R2-CO-HN-R3-NH2 and coupling with 1 mol. of salicylic acid or substitution derivative thereof. The amino-diazo dyestuffs of the above formula may be obtained by coupling resorcinol successively in either order with diazotized R4NH2 and diazotized X-R3-NH2 (X=e.g., nitro or acylamino), converting X into NH2, condensing the product with m- or p-nitrobenzoyl chloride and reducing the nitro group. Alternatively, resorcinol may be coupled successively in either order with diazotized R4NH2 and diazotized O2N-R2-CO-HN-R3-NH2 and the nitro group then reduced. Metallization may be carried out on the intermediates R4X --> resorcinol or the amino-diazo dyestuffs. In the examples: (1) 4-(p-aminobenzamido)-aniline is tetrazotized and coupled first with salicylic acid (or its 4-methyl or 3-chloro derivative) and then with the coppered monoazo dyestuff 2-aminophenol-4-sulphonic acid --> resorcinol; (2) the diamine of (1) is coupled first with salicylic acid and then with the monoazo dyestuff 2-aminophenol-4-sulphonamide --> resorcinol or 2-amino-4-chlorophenol --> resorcinol; (3) 3-(m-aminobenzamido)-aniline is tetrazotized and coupled first with salicylic or cresotic acid and then with the monoazo dyestuff 3 - amino - 4 - oxybenzamide --> resorcinol; 2 - aminophenol - 4 - sulphonamide, 4 - chloro - 2 - aminophenol - 6 - sulphonic acid or 2 - methoxyaniline - 5 - sulphonic acid may also be used to make the monoazo intermediate; (4) 4 - (p - aminobenzamido) - 2 - methylaniline or -2 : 5-dimethoxyaniline is tetrazotized and coupled first with salicylic acid and then with the coppered monoazo dyestuff of (1); (5) 4-acetylamino-aniline is diazotized and coupled with the monoazo dyestuff 2-aminophenol-4-sulphonic acid --> resorcinol; the acetyl group is then hydrolysed off, the product condensed with p-nitrobenzoyl chloride and the nitro group reduced; the amino-disazo dyestuff is then diazotized and coupled with salicylic acid. a further example is given of the dyeing of cotton with the product of (1). Other suitable components are listed.
GB17976/50A 1949-07-20 1950-07-18 Manufacture of trisazo dyestuffs Expired GB682024A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1021520X 1949-07-20

Publications (1)

Publication Number Publication Date
GB682024A true GB682024A (en) 1952-11-05

Family

ID=4553059

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17976/50A Expired GB682024A (en) 1949-07-20 1950-07-18 Manufacture of trisazo dyestuffs

Country Status (3)

Country Link
DE (1) DE849287C (en)
FR (1) FR1021520A (en)
GB (1) GB682024A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1007324B (en) * 1974-02-11 1976-10-30 Acna WATER-SOLUBLE AZO DYES DERIVED FROM 4.4 DIAMINOBENZANILIDE

Also Published As

Publication number Publication date
DE849287C (en) 1952-09-15
FR1021520A (en) 1953-02-19

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