GB442778A - Process for the manufacture of azodyestuffs - Google Patents

Process for the manufacture of azodyestuffs

Info

Publication number
GB442778A
GB442778A GB23475/34A GB2347534A GB442778A GB 442778 A GB442778 A GB 442778A GB 23475/34 A GB23475/34 A GB 23475/34A GB 2347534 A GB2347534 A GB 2347534A GB 442778 A GB442778 A GB 442778A
Authority
GB
United Kingdom
Prior art keywords
pyrazolone
methyl
aminophenyl
acid
product
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
GB23475/34A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB442778A publication Critical patent/GB442778A/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
    • C09B35/02Disazo dyes
    • C09B35/039Disazo dyes characterised by the tetrazo component
    • C09B35/28Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—

Landscapes

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

Abstract

Azo dyes; azo dyes, forming upon the material. --Azo dyestuffs are manufactured by condensing one molecular proportion of a diaminonaphthalenesulphonic acid containing the amino groups neither in onor in peri-position to each other, with two molecular proportions of 4-nitrobenzoyl chloride, reducing the nitro groups, tetrazotizing and coupling with one molecular proportion of 1-(3<1>-aminophenyl)-3-methyl-5-pyrazolone or of 1-(3<1>-aminophenyl)-5-pyrazolone-3-carboxylic acid or an alkyl ester thereof and with one molecular proportion of one of the same coupling components or of a yellow component, free from a diazotizable amino group, selected from the group consisting of phenols, phenol ethers, pyrazolones or the sulphonic or carboxylic acids thereof, b -ketocarboxylic acid arylamides and methyl ketol, the coupling being performed in any sequence. Alternatively, one molecular proportion of a monoacyl derivative of a diaminonaphthalenesulphonic acid of the type specified is condensed one molecular proportion of 4-nitrobenzoyl chloride, the nitro group is reduced, the amino group is diazotized, the diazo compound is coupled with a yellow component of the type specified, the acyl group is split off, the amino group is 4-nitrobenzoylated, the nitro group is reduced to the amino group, and the aminoazo compound is diazotized and coupled with one molecular proportion of 1-(3<1>-aminophenyl)-3-methyl-5-pyrazolone or 1-(3<1>-aminophenyl)-5-pyrazolone-3-carboxylic acid or an alkyl ester thereof. Instead of the aminophenylpyrazolone compounds specified there may be used the corresponding nitro compounds, the nitro group being subsequently reduced. In examples: (1) 2 : 6-diaminonaphthalene-4-sulphonic acid is reacted with 4-nitrobenzoyl chloride in the presence of sodium carbonate, the product is reduced and the resulting di-p-aminobenzoyl-2 : 6-diaminonaphthalene-4-sodium sulphonate is tetrazotized and coupled with 2 mols. of 1 - (3<1>-aminophenyl) - 3 - methyl - 5 - pyrazolone; the product dyes cotton greenish-yellow shades which are not altered by diazotization on the fibre and developing with 1-phenyl-3-methyl-5-pyrazolone, and which yield a yellowish-orange with b -naphthol; (2) di-p-aminobenzoyl-1 : 4-diaminonaphthalene-6-sodium sulphonate, prepared by a method analogous to that of (1), is tetrazotized and coupled with 1 mol. of 1-(6<1>-sulpho - 2<1>-naphthyl) - 3 - methyl - 5 - pyrazolone and 1 mol. of 1-(3<1>-aminophenyl)-3-methpl-5-pyrazolone; the product dyes somewhat more reddish shades than that of (1) ; (3) 1-(4<1>-aminobenzoyl)-4-formyldiaminonaphthalene-6-(or-7-) sodium sulphonate, obtained by reacting 1-amino-4-formylaminonaphthalene-6- (or -7-) sulphonic acid with 4-nitrobenzoyl chloride in the presence of sodium carbonate and reducing the product, is diazotized and coupled with 1-(4<1>-sulphophenyl)-3-methyl-5-pyrazolone, the product, is saponified and condensed with 4-nitrobenzoyl chloride, the nitro group is reduced and the product is diazotized and coupled with 1-(3<1>-aminophenyl)-3-methyl-5-pyrazolone; the product has properties similar to that of (1); (4) di-4-aminobenzoyl-1 : 4-diaminonaphthalene-6-sodium sulphonate is tetrazotized and coupled with 2-mols. of 1-(3<1>-nitrophenyl)-5-pyrazolone-3-carboxylic acid, the nitro groups being subsequently reduced; the product dyes cotton yellow shades which yield an orange on diazotizing and coupling with b -naphthol and a reddish-yellow with 1-phenyl-3-methyl-5-pyrazolone. Samples have been furnished under Sect. 2 (5) of dyestuffs prepared as follows: (A) 1 : 4-naphthylenediamine-6- (or 7-) sulphonic acid is condensed with 4-nitrobenzoyl chloride in the presence of sodium carbonate and the product is reduced, tetrazotized and coupled with salicylic acid and 1-(3<1>-aminophenyl)-3-methyl-5-pyrazolone; (B) the salicylic acid of (A) is replaced by acetoacetic acid anilide. Dyed specimens show the shades obtained on cotton and the effect of diazotization on the fibre and coupling with 1-phenyl-3-methyl-5-pyrazolone and with b -naphthol. Specifications 1441/11, 7303/13, and 3557/14, [all in Class 2 (iii)], are referred to. The Specification as open to inspection under Sect. 91 comprises also the manufacture of azo dyestuffs by condensing one molecular proportion of a monoacyldiaminonaphthalenesulphonic acid of the kind referred to above with one molecular proportion of nitrobenzoyl chloride, reducing the nitro group, diazotizing, coupling with a yellow component free from a diazotizable amino group, splitting of the acyl group by saponification, diazotizing and coupling with one molecular proportion of 1-(3<1>-aminophenyl)-3-methyl-5-pyrazolone or of 1-(3<1>-aminophenyl)-5-pyrazolone-3-carboxylic acid or an ester thereof. This subject-matter does not appear in the Specification as accepted.
GB23475/34A 1933-08-15 1934-08-14 Process for the manufacture of azodyestuffs Expired GB442778A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE442778X 1933-08-15

Publications (1)

Publication Number Publication Date
GB442778A true GB442778A (en) 1936-02-14

Family

ID=6525018

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23475/34A Expired GB442778A (en) 1933-08-15 1934-08-14 Process for the manufacture of azodyestuffs

Country Status (1)

Country Link
GB (1) GB442778A (en)

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