GB677204A - Manufacture of new azo-dyestuffs - Google Patents

Manufacture of new azo-dyestuffs

Info

Publication number
GB677204A
GB677204A GB21016/50A GB2101650A GB677204A GB 677204 A GB677204 A GB 677204A GB 21016/50 A GB21016/50 A GB 21016/50A GB 2101650 A GB2101650 A GB 2101650A GB 677204 A GB677204 A GB 677204A
Authority
GB
United Kingdom
Prior art keywords
acid
amino
group
aminophenyl
oxynaphthyl
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
GB21016/50A
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 GB677204A publication Critical patent/GB677204A/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
    • C09B29/24Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28Amino naphthols
    • C09B29/30Amino naphtholsulfonic acid
    • 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
    • C09B31/00Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02Disazo dyes
    • C09B31/08Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups

Landscapes

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

Abstract

Naphthalene - amino - phenylbenzthiazoles of the formula <FORM:0677204/IV (b)/1> where R is a 2-phenylbenzthiazole residue attached via the phenyl residue and the NHR group is attached in a b -position of the naphthalene ring, are obtained by reacting aminophenyl-benzthiazoles with aminonaphtholsulphonic acids or dihydroxy - naphthalenesulphonic acids in the presence of sulphites. Examples show the production of 2-[41-(511-oxynaphthyl - 211 - aminophenyl)] - 6 - methylbenzthiazole - X : 711 - disulphonic acid, 2-[41 - (811 - oxynaphthyl - 211 - aminophenyl)]-6 - methylbenzthiazole - X : 611 - disulphonic acid and 2 - [41 - (811 - oxynaphthyl - 211-aminophenyl)] - 6 - methylbenzthiazole - 611-sulphonic acid, X indicating that the position of attachment to the phenylbenzthiazole nucleus is uncertain. Other products are listed; the phenyl residue may carry a methyl substituent. The starting materials are obtained by acylating 2-amino-thiophenol with nitrobenzoyl chloride, ring-closing with hydrochloric acid, sulphonating, reducing the nitro group to an amino group and again sulphonating if desired.ALSO:The invention comprises azo dyestuffs of the formula <FORM:0677204/IV (c)/1> where R1 is the residue of a diazo component, R is a 2-phenylbenzthiazole residue attached via the phenyl group and -NHR is in one of the b -positions in the naphthalene ring. R1 preferably contains an o-metallizable group, e.g. hydroxy, methoxy or carboxy, together with an o-hydroxy-carboxylic group if desired. R1 may be of the benzene or naphthalene series and may contain a further arylazo group. The phenylbenzthiazole residue may be substituted, e.g. by methyl or sulphonic acid groups. When R1 contains an amino group (or acylamino converted thereto by hydrolysis), two mols. of the dyestuff or one mol. of this and one mol. of another aminoazo dyestuff may be linked together with phosgene or a halogen substituted heterocyclic compound, e.g. cyanuric chloride or dichloroquinazoline. Similarly, when R1 contains a nitrogroup, two mols. may be linked by reducing the nitro groups to azo or azoxy, or alternatively the nitrogroups may be reduced to amino and reacted as above. The products dye cellulosic fibres such as linen, cotton, artificial silk or staple fibre from regenerated cellulose. They may be metallised (especially coppered) in substance, in the dyebath or on the fibre, e.g. by the process of Specification 455,274 or 644,883. In the examples: (1) the dyestuff 2-aminophenol-4-sulphonamide --> 2-[41-(511-oxynaphthyl-211-aminophenyl)] - 6 - methylbenzthiazole disulphonic acid is prepared and coppered; (2) 5-amino-salicylic acid is diazotized and coupled with the same component; (3) tetrazotized benzidine is coupled with one mol. of salicylic acid and one mol. of 2-[31- or 41-(811-oxynaphthyl - 211-aminophenyl)] - 6 - methylbenzthiazole disulphonic acid; (4) 4-amino-41-hydroxyazobenzene-31-carboxylic acid is diazotized and coupled with the components of (3); (5) 4 - amino - 41 - hydroxyazobenzene - 3 : 31-dicarboxylic acid is diazotized and coupled with 2 - [41 - (811 - oxynaphthyl - 211 - aminophenyl - 6 - methylbenzthiazole - 611 - sulphonic acid; (6) 5-nitro-anthranilic acid is diazotized and coupled with the 41-component of (3); the product is reduced with glucose and alkali, and may be coppered if desired; (7) the nitro-dyestuff of (6) is reduced with sodium sulphide and reacted with one mol. of phosgene together with one mol. of 4-amino-41-hydroxyazobenzene-31-carboxylic acid; (8) as in (6) using as diazo component 5-nitro-2-aminoanisole; coppering may precede reduction; (9) the dyestuff 8-(p-chlorobenzenesulphonyloxy) - 1 - naphthylamine-3 : 6-disulphonic acid --> 4-methoxy-m-toluidine is diazotized and coupled with the component of (1) or (6) and the sulphonic ester group then hydrolysed; (10) cotton is dyed with the product of example (3)-41-isomer-and after-coppered in one of three ways. Various other substituted anilines, naphthylamines and p-aminoazobenzenes are specified as diazo components, including the dyestuffs 2-naphthylamine-4 : 8-disulphonic acid --> and 1-amino-8 - naphthol - 3 : 6 - disulphonic acid --> 4-methoxy-m-toluidine. Other coupling components are mentioned.
GB21016/50A 1949-08-25 1950-08-24 Manufacture of new azo-dyestuffs Expired GB677204A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH677204X 1949-08-25

Publications (1)

Publication Number Publication Date
GB677204A true GB677204A (en) 1952-08-13

Family

ID=4528206

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21016/50A Expired GB677204A (en) 1949-08-25 1950-08-24 Manufacture of new azo-dyestuffs

Country Status (1)

Country Link
GB (1) GB677204A (en)

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