GB811521A - Monoazo dyestuffs of the benzeno-azo-naphthalene series and metal complexes thereof - Google Patents
Monoazo dyestuffs of the benzeno-azo-naphthalene series and metal complexes thereofInfo
- Publication number
- GB811521A GB811521A GB22408/56A GB2240856A GB811521A GB 811521 A GB811521 A GB 811521A GB 22408/56 A GB22408/56 A GB 22408/56A GB 2240856 A GB2240856 A GB 2240856A GB 811521 A GB811521 A GB 811521A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dyestuffs
- bis
- ethyl
- hydroxy
- cyano
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The preparation by conventional methods of 1 - acetylamino - 3,6 - di - (dimethyl - and hydroxyethyl) sulphamyl - and 1 - benzoylamino - 3,6 - di - sulphamyl - 8 - naphthols is described via the sulphochlorides from the corresponding sulphonic acids. 2-Aminophenol-4-sulphonmorpholide is made by converting 2-nitro-1-chlorobenzene to the 4-sulphochloride, the latter to the corresponding sulphonmorpholide, subsequent hydrolysis of the chloro-group, and final reduction to the amine. The products are dyestuff intermediate vide Group IV (c). Specification 326,226, [Class 2 (iii)], is referred to.ALSO:The invention comprises dyestuffs of formula: <FORM:0811521/IV (c)/1> where X is H or Hlg, R1 and R2 are H, alkyl or hydroxy- or cyano-alkyl or may be linked to form a heterocyclic ring and R3 is H, acyl or sulphonyl and their 1,2-metal complexes. Listed values for R1 and R2 are methyl, ethyl, n- and iso-propyl-, n-butyl, hydroxy-ethyl, -propyl and -butyl, cyano-ethyl and -propyl and sulphon-morpholide and for R3 are acetyl, propionyl, butyryl, benzoyl and phenyl- and methyl-sulphonyl. The dyestuffs may be made in conventional fashion from appropriate 2-aminophenols and aminophthols and metallized in the usual way to yield 1,2-complexes. In the formation of the complexes the starting dyestuffs may comprise the o-alkoxy or -acyl-o1-hydroxy-dyestuffs corresponding to those of the above formula. Specified 2-aminophenols are 2 - aminophenol - 4 - N,N - dimethyl -, -diethyl-, -di-isopropyl-, -bis-hydroxy- and -cyano-ethyl, bis-hydroxypropyl-, N-cyano- and -hydroxy - ethyl -, 2 - amino - 6 - bromophenol-4 - N - ethyl, - N,N - dimethyl - and - diethyl-, 2 - amino - - 8 chlorophenol - 4 - N - hydroxyethyl-, -methyl-, -N,N-dimethyl-, -diethyl-, -diisopropyl-and -bis-hydroxy- and -cyano-ethyl-sulphonamides and 2-amino-6-chlorophenol-4-sulphonamide. Specified coupling components are 1 - benzenesulphonylamino - 3,6 - dimorpholino- and -diethyl-sulphamyl- and -bis-(diethylsulphamyl)-, 1-methylsulphonylamino-3,6-di - (diethylsulphamyl)-, 1 - acetylamino - 3,6-bis - (dimethyl -, - di - (cyanoethyl) -, and -hydroxy- and -cyano-ethyl-sulphamyl)-, 1-propionylamino - 3,6 - diethylsulphamyl -, 1 - benzoylamino - 3,6 - dimorpholino - and - disulphamyl- and -bis-(dihydroxyethyl-, -cyanoethyl-and -diethyl-sulphamyl)- and 1-amino-3,6 - bis - dimethylsulphamyl - 8 - naphthols. Indicated metals for complex formation are those of atomic weights 52-66, e.g. copper, nickel and iron and especially chromium and cobalt. Dyeing may be effected with the metal dyestuffs in substance, on a substratum or in situ organic fibrous materials being dyed in violet to blue shades. Dyeing is preferably carried out with the dyestuffs in a dispersed form. Listed materials for dyeing include nitrogenous and cellulosic materials. Synthetic resins, organic solvents, stains, varnishes and lacquers may be coloured. Examples are provided of the preparation of the dyestuffs and the use of their chromium and cobalt complexes in dyeing processes the dyestuff components used being selected from those listed above with the addition of 2-aminophenol-4 - sulphonamide, - 4 - N - ethylsulphonamide and -4-sulphonmorpholide and finished chromium dyestuffs derived from 1-acetylamino-3,6 - bis - dimethyl and N - hydroxyethyl - sulphonamido - 8 - naphitols are hydrolysed to the corresponding 1-amino-dyestuffs. Specification 326,226, [Class 2 (iii)], is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US811521XA | 1955-08-25 | 1955-08-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB811521A true GB811521A (en) | 1959-04-08 |
Family
ID=22162412
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22408/56A Expired GB811521A (en) | 1955-08-25 | 1956-07-19 | Monoazo dyestuffs of the benzeno-azo-naphthalene series and metal complexes thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB811521A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3153642A (en) * | 1959-12-22 | 1964-10-20 | Carbochimique Sa | Azo dyestuffs containing a beta-cyanoethyl, alkyl amino sulfonyl group |
-
1956
- 1956-07-19 GB GB22408/56A patent/GB811521A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3153642A (en) * | 1959-12-22 | 1964-10-20 | Carbochimique Sa | Azo dyestuffs containing a beta-cyanoethyl, alkyl amino sulfonyl group |
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