GB313110A - Process for the manufacture of azo-dyestuffs - Google Patents

Process for the manufacture of azo-dyestuffs

Info

Publication number
GB313110A
GB313110A GB713128A GB713128A GB313110A GB 313110 A GB313110 A GB 313110A GB 713128 A GB713128 A GB 713128A GB 713128 A GB713128 A GB 713128A GB 313110 A GB313110 A GB 313110A
Authority
GB
United Kingdom
Prior art keywords
acid
dyestuff
amino
sulphonic
phenoxy
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
GB713128A
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
Priority to GB713128A priority Critical patent/GB313110A/en
Publication of GB313110A publication Critical patent/GB313110A/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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling

Landscapes

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

Abstract

313,110. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.), March 7, 1928. Azo dyes; lakes.-Azo dyes containing substituted or unsubstituted arylhydroxy fatty acid residues attached to nitrogen atoms are made by coupling a diazo compound with a component which is substituted by the arylhydroxy fatty acid residue, or by coupling a diazotized phenylenediamine containing an arylhydroxy fatty acid residue attached to the second amino group or a derivative thereof, or by introducing the arylhydroxy fatty acid residue into an amino group of an azo dyestuff. They are suitable for discharge printing on wool and for the production of lakes. According to examples, (1) diazotized aniline is coupled with 1-phenoxyacetamino-8- hydroxynaphthalene - 3 : 6 - disulphonic acid. Instead of aniline, 2-aminobenzoic acid, 2-acetamino-5-aminoanisole, 4-amino-acetanilide or pxylidine may be used. The phenoxyacetyl residue may be replaced by the 2-(or 4)-chlorphenoxyacetyl-, the 2-(or 4)-nitrophenoxyacetyl-, the 2- chloro-4-methylphenoxypropionyl or the 1-(or 2-)- naphthoxyacetyl residue, and H acid by other aminonaphtholsulphonic acids or 1-ethylamino-8-hydroxynaphthalene-3 : 6-disulphonic acid. The dyestuff aniline # 1-(4<1>-chlorophenoxyacetyl-) - amino-8-hydroxynaphthalene - 4 : 6 - disulphonic acid dyes wool yellowish red. The dye-stuff aniline # H acid (alkaline), treated with phenoxyacetylchloride, yields the dyestuff first mentioned in this example. (2) The dyestuff 4-nitro-1-aminobenzene-2-sulphonic acid # 2- (#-amincethylamino)naphthalene-7-sulphonic acid is treated with 2-chlorophenoxyacetylchloride or the same final dyestuff is obtained from diazotized 4-nitro-1-aminobenzene-2-sulphonic acid coupled with 2-(#-2<1> -chlorophenoxyacetylaminoethylamino-) naphthatene-7-sulphonic acid. It dyes wool reddish violet. The dyestuff 4 : 6-dinitro-1-aminobenzene-2-sulphonic acid # 2-(#- 4<1>-methylphenoxyacetylaminoethylamino-) - naphthatene-6-sulphonic acid or 2-(#-5<1>chlor-2<1>-methylphenoxy - # - propionylaminoethylamino-) - naphthalene-7-sulphonic acid dyes wool reddish blue. (3) The dyestuff aniline-2 : 5-disulphonic acid # p-xylidine # 1-(4<1>-chlorophenoxyacetylamino)-8- hydroxynaphthalene 4 : 6-disulphonic acid gives a clear violet lake, and the dyestuff 4-chlor-2- anisidine # 1-(4<1>-chlorophenoxyacetylamino-)- 8-hydroxynaphthalene-4:6-disulphonic acid is a bluish red. (4) The dyestuff 4-amino-1-phenoxyacetylaminobenzene # 1-(4<1>-sulpho)-phenyl-3- methyl-5-pyrazolone dyes wool golden yellow. The phenoxyacetyl residue may be replaced by the 2-(or 4-)-chlorophenoxyacetyl-, the 2-(or 4-)- nitrophenoxyacetyl-, the #-(2-methylphenoxy-)- propionyl-, or the 1-(or 2)-naphthoxyacetyl residues. 2 - Amino - 4 - phenoxyacetylamino - 1 - methoxybenzene, 4 amino-2-N-methyl-N-phenoxyacetylamino-1-methylbenzene or 4-amino-1-N- ethyl-N-phenoxy-acetylaminobenzene, when diazotized and coupled with 2-methylamino-8-hydroxynaphthalene-6-sulphonic acid, give brown shades. Other pyrazolones, methylketol and its sulphonic acids or aminonaphthol sulphonic acids and their N-alkyl or acidyl substitution products may be used as coupling components. The nitro-group in the dyestuff 4-nitraniline # (4<1>-sulpho-)-1- phenyl-3-methyl-5-pyraxolone is reduced and treated with phenoxyacetylohloride. (5) The dyestuff 4-amino-1-phenoxyacetylamino-benzene # 1-naphthol-3 : 6-disulphonic acid dyes wool yellowish red. The dyestuff 2-(N-phenoxyacetylamino-N-ethyl)-1-aminobenzene # 2-naphthol- 6 : 8-disulphonic acid dyes wool orange. 4-Amino- (phenoxyacetylanilide)-3-sudphonic acid, 4-amino- (2<1>-naphthoxyacetylanilide)-3-sulphonic acid or 3 : 5-dichlor - 4 - amino-(phenoxypropionylanilide) may also be used as diazo components. Phenoxy, or naphthoxyacylated aminonaphthol sulphonic acids are prepared from the corresponding aminonaphthol sulpho acid and the corresponding substituted or unsubstituted phenoxy- or naphthoxy-acyl chloride. Substituted phenoxy- or naphthoxy-acetyl- or propionyl-chlorides are prepared by treating the corresponding acid with thionyl chloride. Substituted phenoxy- or naphthoxy-acetic or propionic acids are prepared from the sodium salts of the corresponding phenols or naphthols and the sodium salt of chloracetic or #-chloropropionic acid. 2-(#-Substituted phenoxyacetyl- or #-propionylaminoethylamino-)-naphthalene sulphonic acids are prepared from the corresponding 2-(#-aminoethylamino-)-naphthalene sulphonic acid and the corresponding substituted phenoxyacetyl- or #- propionyl-chloride. Phenoxy- or naphthoxyacetyl -1 : 4- or 1: 3- phenylene diamines are prepared by phenoxy- or naphthoxyacetylating the corresponding nitro aminobenzene followed by reduction of the nitro group, or from the diamino compound and one molecular part of the acetylating agent.
GB713128A 1928-03-07 1928-03-07 Process for the manufacture of azo-dyestuffs Expired GB313110A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB713128A GB313110A (en) 1928-03-07 1928-03-07 Process for the manufacture of azo-dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB713128A GB313110A (en) 1928-03-07 1928-03-07 Process for the manufacture of azo-dyestuffs

Publications (1)

Publication Number Publication Date
GB313110A true GB313110A (en) 1929-06-07

Family

ID=9827195

Family Applications (1)

Application Number Title Priority Date Filing Date
GB713128A Expired GB313110A (en) 1928-03-07 1928-03-07 Process for the manufacture of azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB313110A (en)

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