GB562762A - New azo dyestuffs - Google Patents

New azo dyestuffs

Info

Publication number
GB562762A
GB562762A GB969842A GB969842A GB562762A GB 562762 A GB562762 A GB 562762A GB 969842 A GB969842 A GB 969842A GB 969842 A GB969842 A GB 969842A GB 562762 A GB562762 A GB 562762A
Authority
GB
United Kingdom
Prior art keywords
acid
diphenylpyrrole
pyrrole
nitro
phenyl
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
GB969842A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB969842A priority Critical patent/GB562762A/en
Publication of GB562762A publication Critical patent/GB562762A/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
    • C09B39/00Other azo dyes prepared by diazotising and coupling

Landscapes

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

Abstract

Azo dyes are obtained by coupling a diazotised arylamine with a 2 : 4-diarylpyrrole, which may be substituted in the 3-position. When the diazo component carries a metal-complex-forming group in o-position to the amino group, the products are capable of conversion into metal complex compounds in substance or on the fibre. The products containing one or more sulphonic acid or other solubilizing groups are suitable for dyeing wool and, in some cases, cotton. Those free from solubilizing groups are applicable as pigments. Specified diazo components are 3-chloroaniline, 4- or 5-nitro-2-aminoanisole, 2 : 5 - dichloroaniline, 3 - amino - carbazole, 4 - benzoylamino - 2 : 5 - dimethoxy - aniline, 3 - nitro - 4 - aminotoluene, 5 - nitro - 2 - aminotoluene, 2-nitro-4-chloroaniline, 4-chloro-2-aminotoluene, aniline-2 : 5-disulphonic acid, 4 : 6 - dinitro - 2 - aminophenol, picramic acid, 2 - chloro - 4 - aminophenetole, 4-aminodiphenyl, 4 - chloro - 2 - aminophenol and its 6 - sulphonic acid, anthranilic acid and its 4-sulpho derivative, 4- or 5-nitro-2-aminophenol, 1-aminonaphthalene, 1-aminoanthraquinone, 1 : 2-aminonaphthol-4-sulphonic acid, benzidine and its 3 : 31-dichloro, 3 : 31-dicarboxy, 2 : 21-disulpho and 3 : 31-di-(carboxymethoxy) derivatives, dianisidine, 4 : 41 - diaminodiphenylamine, 4 : 41 - diaminobenzanilide-31-carboxylic acid, 4 : 41-diaminostilbene-2 : 21-disulphonic acid, 3-nitro4 - aminotoluene \sQ cresidine, 4 - aminoazo - benzene -41-sulphonic acid and 3-amino-2 : 4-diphenylpyrrole. Specified coupling components are 2 : 4 - diphenylpyrrole, 2 - phenyl - 4 - (p - methoxyphenyl) -pyrrole, 2-(p-methoxyphenyl)-4 - phenyl - pyrrole, 2 - (m - hydroxyphenyl) - 4 - phenyl - pyrrole, 2 - (o - chlorophenyl) - 4 - phenyl - pyrrole, 2 - (p - acetylaminophenyl) - 4 - phenyl - pyrrole, 2 - (a - naphthyl) - 4 - phenyl - pyrrole, 2 - phenyl - 4 - (b - naphthyl) - pyrrole and 2 : 3 : 4 - triphenylpyrrole (cf. Specifications 554,102 and 556,156), the 3-benzoylamino, 3-acetylamino and 3-acetoacetylamino derivatives of 2 : 4-diphenylpyrrole, 3 - benzoylamino - 2 : 4 - di - (p - tolyl) -pyrrole and the mono- and di-sulphonic acids of 2 : 4-diphenylpyrrole (cf. Specification 562,753). Examples relate to the production of the dyestuffs, (1) aniline-2 : 5-disulphonic acid \sQ 2 : 4-diphenylpyrrole, which dyes wool, from an acid bath, orange-brown; (2) 4-chloro-2-aminotoluene or 3-nitro-4-aminotoluene \sQ 2 : 4-diphenylpyrrole or 3 : 31-dichlorobenzidine \sQ 2 : 4-diphenylpyrrole (2 mols.), which are pigments; (3) 4 : 6-dinitro-2-aminophenol \sQ the monosulphonic acid of 2 : 4-diphenylpyrrole, which is suitable for dyeing wool by the metachrome or the after-chrome process; (4) benzidine or 4 : 41-diaminostilbene-2 : 21-disulphonic acid \sQ the disulphonic acid of 2 : 4-diphenylpyrrole (2 mols.), which are suitable for dyeing cotton; (5) 4-aminoazobenzene-41-sulphonic acid \sQ the disulphonic acid of 2 : 4-diphenylpyrrole, which dyes cotton bluish red; (6) 4 : 41 - diamino - 3 : 31 - di - (carboxymethoxy) - diphenyl \sQ the disulphonic acid of 2 : 4-diphenylpyrrole (2 mols.), which dyes cotton bluish violet, becoming blue on after-coppering; (7) 4 : 41 - diamino - 3 : 31 - dicarboxy - diphenyl \sQ the disulphonic acid of 2 : 4-diphenylpyrrole (2 mols.), which dyes cotton violet, becoming greenish blue on after-coppering; (8) 4 : 41 - diaminobenzanilide - 31 - carboxylic acid \sQ the disulphonic acid of 2 : 4-diphenylpyrrole (2 mols.), which dyes cotton reddish orange, becoming dull violet on after-coppering; (9) 4 : 41-diaminobenzanilide-31-carboxylic acid \sQ salicylic acid (1 mol.) and the disulphonic acid of 2 : 4-diphenylpyrrole (1 mol.), which dyes cotton reddish orange, becoming grey on after-coppering. 4 : 41-Diaminobenzanilide - 31 - carboxylic acid is obtained by reduction of the condensation product from 6-nitro-3-aminobenzoic acid and 4-nitrobenzoyl chloride. 3 - Acylamino - 2 : 4 - di - p - tolyl - pyrroles are obtained by acylation with the appropriate acid halide or anhydride of 3-amino-2 : 4-di-p-tolylpyrrole, obtained by treating with mineral acid the anhydro-bis-phenacylamine resulting from the action of alkali on the salt of 4-methyl-aminoacetophenone resulting from the reduction of the product of reaction of amyl nitrite with 4-methylacetophenone.
GB969842A 1942-07-13 1942-07-13 New azo dyestuffs Expired GB562762A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB969842A GB562762A (en) 1942-07-13 1942-07-13 New azo dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB969842A GB562762A (en) 1942-07-13 1942-07-13 New azo dyestuffs

Publications (1)

Publication Number Publication Date
GB562762A true GB562762A (en) 1944-07-14

Family

ID=9877039

Family Applications (1)

Application Number Title Priority Date Filing Date
GB969842A Expired GB562762A (en) 1942-07-13 1942-07-13 New azo dyestuffs

Country Status (1)

Country Link
GB (1) GB562762A (en)

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