GB781484A - New disazo-dyestuffs and process for making them - Google Patents
New disazo-dyestuffs and process for making themInfo
- Publication number
- GB781484A GB781484A GB29265/54A GB2926554A GB781484A GB 781484 A GB781484 A GB 781484A GB 29265/54 A GB29265/54 A GB 29265/54A GB 2926554 A GB2926554 A GB 2926554A GB 781484 A GB781484 A GB 781484A
- Authority
- GB
- United Kingdom
- Prior art keywords
- naphthol
- acid
- group
- phenylamino
- sulphonic acid
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/26—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of a diaryl urea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyestuffs of formula: <FORM:0781484/IV (b)/1> where X1 and X2 are phenylamino groups at least one of the phenyl residues of which contain a group imparting solubility in water. They may be made by treating a monoazo dyestuff of formula: <FORM:0781484/IV (b)/2> X being a phenylamino group containing in the phenyl residue a group imparting solubility in water with phosgene advantageously in a weak aqueous alkaline medium. The monoazo dyestuff may be made by coupling a diazotized 1-amino - 4 - nitro - o acetylamino - benzene - 2-carboxylic and in an alkaline, preferably weakly alkaline, medium with the appropriate 2-phenylamino - 5 - oxynaphthalene - 7 - sulphonic acid and converting the 4-substituent into an amino group. Two different naphthol sulphuric acids may be linked by means of phosgene to provide asymmetrical disazo dyestuffs although symmetrical dyestuffs are preferred. The disazo dyestuffs may also be made by coupling tetrazotized 4,41 - diaminodiphenyl - urea - 3,31 - dicarboxylic acid in an alkaline medium with the appropriate naphthol sulphonic acid or acids. Groups specified as imparting solubility in water are sulphonamide, carbomethoxy, carboxylic acid and sulphonic acid groups. The dyestuffs dye many materials especially cellulosic materials, e.g. cotton, linen and artificial silk or regenerated cellulose. The dyeings may be treated with an agent yielding metal, especially copper, on the fibre, in the dyebath or partially on the fibre and partially in the dyebath as in Specification 455,274, [Group IV]. The coppered dyeings yield violet shades. In examples: (1) 4 - nitro - 1 - aminobenzene - 2 - carboxylic acid is diazotized, coupled with 2-phenylamino-5-naphthol - 7 - sulphonic acid - 31 - sulphonic acid amide, the nitro group in the monoazo dyestuff thus obtained is reduced to an amino group with sodium hydrosulphide and the product reacted with urea to give a disazo dyestuff also obtainable by indirectly tetrazotizing 4,41-diamino - diphenyl - urea - 3,31 - dicarboxylic acid and coupling with the naphthol 7-sulphonic acid; (2) 1-amino-4-acetylaminobenzene-2-carboxylic acid is diazotized, coupled with 2-(41-carboxymethoxyphenylamino) - 5 - naphthol - 7 - sulphonic acid, the acetylamino group in the monoazo dyestuff thus prepared is hydrolysed with caustic soda and the product treated with urea to yield the desired disazo dyestuff; (3) 4,41 - diaminodiphenylurea - 3,31 - dicarboxylic acid is tetrazotized and coupled with a mixture of 2 - phenylamino - and 2 - (41 - carboxymethoxy - phenylamino) - 5 - naphthol - 7 - sulphonic acid to yield an asymmetrical dyestuff; (4) diazotized 1 - amino - 4 - acetylaminobenzene - 2 - carboxylic acid is coupled with 2-(41 - aminophenylamino) or (41 - methyl phenylamino) - 5 - naphthol - 7,31 - disulphonic acid, or 2-phenylamino-5-naphthol-7-sulphuric acid-31-carboxylic acid, the acetylamino group in the monoazodye-stuff thus obtained is hydrolysed with caustic soda and the product treated with phosgene to yield a disazo dyestuff; (5) 4-nitro-1-aminobenzene-2-carboxylic acid is diazotized, coupled with 2 - (41 - chlorophenylamino)-5-naphthol-7,31-disulphonic acid and the nitro group reduced and the urea formed as in (1) and in (6) 4,41-diaminodiphenylurea-3,31-dicarboxylic acid is tetrazotized and coupled with 2 - (41 - chlorophenylamino) - 5 - naphthol - 7,31-disulphonic acid.ALSO:2 - Phenylamino - 5 - naphthol - 7 - sulphonic acids containing a sulphonamide group in the phenyl nucleus used as coupling components in the preparation of azo dyestuffs, cf. Group Group IV(c), are made by treating 2-amino-5-oxy- or 2,5-dioxy-naphthalene-7-sulphonic acid with an aminobenzene sulphonic acid amide in the presence of a sulphite. In Example (1) the above sulphonic acids are treated with aniline-3-sulphonic acid amide in the presence of an alkaline solution of sodium bisulphite to yield 2-phenylamino-5-naphthol-7-sulphonic acid-31-sulphonic acid amide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH781484X | 1953-10-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB781484A true GB781484A (en) | 1957-08-21 |
Family
ID=4536255
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29265/54A Expired GB781484A (en) | 1953-10-26 | 1954-10-11 | New disazo-dyestuffs and process for making them |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB781484A (en) |
-
1954
- 1954-10-11 GB GB29265/54A patent/GB781484A/en not_active Expired
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