GB440113A - Process for the manufacture of azodyestuffs - Google Patents

Process for the manufacture of azodyestuffs

Info

Publication number
GB440113A
GB440113A GB1828034A GB1828034A GB440113A GB 440113 A GB440113 A GB 440113A GB 1828034 A GB1828034 A GB 1828034A GB 1828034 A GB1828034 A GB 1828034A GB 440113 A GB440113 A GB 440113A
Authority
GB
United Kingdom
Prior art keywords
aminobenzothiazole
methoxy
cellulose acetate
shades
hydroxynaphthoquinoline
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
GB1828034A
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 GB1828034A priority Critical patent/GB440113A/en
Publication of GB440113A publication Critical patent/GB440113A/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
    • C09B29/0025Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds

Landscapes

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

Abstract

Azo dyes; azo dyes, forming upon the material; cellulose esters, dyeing.--Azo dyes are manufactured by coupling a diazotized 2-aminothiazole compound with an amine coupling in p-position to the amino group, including such amines in which the nitrogen atom of the amino group is part of a heterocyclic ring. The products are suitable for dyeing and printing cellulose esters, e.g. cellulose acetate artificial silk. The dyestuffs containing a primary amino group may be diazotized on the fibre and developed. Examples describe the manufacture of the following dyestuffs: (1) 6-methoxy-2-aminobenzothiazole --> dihydroxyethyl-m-toluidine; the product dyes cellulose acetate pink shades; (2) 6-methoxy-2-aminobenzothiazole --> dihydroxyethylaniline; the product dyes cellulose acetate red shades; the dihydroxyethylaniline may be replaced by methylhydroxyethylaniline, ethylhydroxyethylaniline, diethylaniline, dimethylaniline, cresidine CH3 : NH2 : OCH3 = 1 : 2 : 4), xylidine (CH3 : CH3 : NH2 = 1 : 4 : 2), dihydroxyethylcresidine, dihydroxyethyl - m - chloraniline or dihydroxyethylaminohydroquinone dimethyl ether, and the 6 - methoxy - 2 - aminobenzothiazole by 6 - ethoxy-, 6 - chloro-, 6 - methyl-, 4 - chloro-6-methyl- or 6-nitro-2-aminobenzothiazole; (3) 4 - methyl - 2 - aminothiazole --> dihydroxyethylaniline; the product dyes cellulose acetate yellowish-red shades; (4) the 2-aminothiazole obtained from tetrahydro-b -naphthylamine (by transforming it into the corresponding thiourea and oxidizing this with sulphuryl chloride) --> methylhydroxyethylaniline; the product dyes cellulose acetate bluish-red shades; (5) 2-aminobenzothiazole --> 1-amino-3-methyl-6-methoxybenzene; the product dyes cellulose acetate scarlet shades, which may be diazotized on the fibre and developed with 2 : 3-hydroxynaphthoic acid, yielding a blue; (6) 6-methoxy-2-aminobenzothiazole --> 1 - hydroxyethylamino - 5-hydroxynaphthalene; the product dyes cellulose acetate blue shades; the 6-methoxy-2-aminobenzothiazole may be replaced by 2-aminobenzothiazole itself or by other substitution products thereof, and the 1-hydroxyethylamino-5-hydroxynaphthalene by 1-amino-5-hydroxynaphthalene, 1-(g -chloro-2-hydroxypropyl) - amino - 5 - hydroxynaphthalene or 1 - dimethylamino - 5 - hydroxynaphthalene ; (7) 6 - methoxy - 2 - aminobenzothiazole --> py - 3 - hydroxytetrahydro - 7 - hydroxynaphthoquinoline; the product dyes cellulose acetate bluish-green shades; the 6-methoxy-2-aminobenzothiazole may be replaced by 2-aminobenzothiazole; (8) 6-methoxy-2-aminobenzothiazole --> py-tetrahydro-3-hydroxynaphthoquinoline; the product dyes cellulose acetate reddish-blue shades; (9) 6-methoxy-2-aminobenzothiazole --> py-3-hydroxytetrahydro-7-hydroxynaphthoquinoline; the product dyes cellulose acetate bluish-green shades; (10) 6 - methoxy - 2 - aminobenzothiazole --> N-phenylpiperazine; the product dyes cellulose acetate red shades; (11) 6-methoxy-2-aminobenzothiazole --> py - tetrahydro - 1 - butyl - 3-hydroxy-7-methylquinoline; the product dyes cellulose acetate reddish-violet shades; (12) 6 - methoxy - 2 - aminobenzothiazole --> 1-hydroxyethyl-3-hydroxytetrahydro-7-hydroxynaphthoquinoline; the product dyes cellulose acetate bluish-green shades; the 6-methoxy-2-aminobenzothiazole may be replaced by 2-aminobenzothiazole or its 6-methyl derivative. Dihydroxyethylcresidine, dihydroxyethyl - m - chloraniline and dihydroxyethylaminohydroquinone dimethyl ether are obtained by heating in water one molecular proportion of cresidine, m-chloraniline and aminohydroquinone dimethyl ether respectively with two molecular proportions of glycol chlorhydrin in the presence of prepared chalk. 4 - Chloro - 6 - methyl - 2 - aminobenzothiazole is obtained by transforming 2-chloro-4-methylaniline hydrochloride by means of ammonium thiocyanate into the corresponding thiourea and oxidizing this with sulphuryl chloride. 1 - Hydroxyethylamino - 5 - hydroxynaphthalene is obtained by heating in water 1-amino-5-naphthol with glycol chlorhydrin in the presence of prepared chalk. 1 - (g - Chloro - 2 - hydroxypropyl) - amino - 5 - hydroxynaphthalene is obtained by boiling in methyl alcohol 1-amino-5-naphthol and epichlorhydrin. py - 3 - Hydroxytetrahydro - 7 - hydroxynaphthoquinoline is obtained by boiling in butyl alcohol 1-amino-5-naphthol and epichlorhydrin. py - Tetrahydro - 3 - hydroxynaphthoquinoline hydrochloride is obtained by boiling in water a -naphthylamine and epichlorhydrin. py - Tetrahydro - 1 - butyl - 3 - hydroxy - 7 - methylquinoline is obtained by heating 1-butylamino-3-methylbenzene with epichlorhydrin in chlorobenzene. 1 - Hydroxyethyl - 3 - hydroxytetrahydro - 7 - hydroxynaphthoquinoline is obtained by heating in water py-3-hydroxytetrahydro-7-hydroxynaphthoquinoline with glycol chlorhydrin in the presence of prepared chalk.
GB1828034A 1934-06-20 1934-06-20 Process for the manufacture of azodyestuffs Expired GB440113A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1828034A GB440113A (en) 1934-06-20 1934-06-20 Process for the manufacture of azodyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1828034A GB440113A (en) 1934-06-20 1934-06-20 Process for the manufacture of azodyestuffs

Publications (1)

Publication Number Publication Date
GB440113A true GB440113A (en) 1935-12-20

Family

ID=10109758

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1828034A Expired GB440113A (en) 1934-06-20 1934-06-20 Process for the manufacture of azodyestuffs

Country Status (1)

Country Link
GB (1) GB440113A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2659719A (en) * 1951-06-23 1953-11-17 Eastman Kodak Co 2-amino-5-nitrothiazole azo dye compounds
DE1135593B (en) * 1958-11-03 1962-08-30 Ici Ltd Process for the production of water-insoluble azo dyes
DE1135594B (en) * 1958-12-03 1962-08-30 Ici Ltd Process for the preparation of water-insoluble azo dyes

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2659719A (en) * 1951-06-23 1953-11-17 Eastman Kodak Co 2-amino-5-nitrothiazole azo dye compounds
DE1135593B (en) * 1958-11-03 1962-08-30 Ici Ltd Process for the production of water-insoluble azo dyes
DE1135594B (en) * 1958-12-03 1962-08-30 Ici Ltd Process for the preparation of water-insoluble azo dyes

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