GB684527A - New disazo-dyestuffs and process for their manufacture - Google Patents
New disazo-dyestuffs and process for their manufactureInfo
- Publication number
- GB684527A GB684527A GB29513/50A GB2951350A GB684527A GB 684527 A GB684527 A GB 684527A GB 29513/50 A GB29513/50 A GB 29513/50A GB 2951350 A GB2951350 A GB 2951350A GB 684527 A GB684527 A GB 684527A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- acid
- diazotized
- salicylic
- nitro group
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Amino-salicylic acids which may contain a sulphonic acid group are condensed with m- or p-nitrobenzoyl chloride to form nitrobenzoyl-amino-salicylic acids, and the nitro group then reduced to amino. The nuclei may contain further substituents other than carboxylic acid or sulphonic acid groups. Specified starting materials are 3-amino-5-sulphosalicylic acid, 5-amino-4-sulphosalicylic acid and 5-amino-3-sulphosalicyclic acid. Specifications 555,791, 583,849 and 619,969 are referred to.ALSO:The invention comprises disazo dyestuffs of the formula R1-N = N-R2-NH-CO-R3-NH-CO-NH-R4-N = N-R5 or R1-NH-CO-R3-N = N-R2-NH-CO-NH-R4-N = N-R5, in which R1-R5 are benzene nuclei; R1 and R5 are salicylic acid residues; the linkages to R2 and R4 are para and to R3 are meta or para; R4 contains a chlorine atom ortho to the azo group; one sulphonic acid group is present on R1 or R2 in the first formula and on R1 in th second formula; there are no carboxylic acid or sulphonic acid groups other than those stated above. The dyestuffs are made by reacting phosgene with one mol. of NH2-R4-N = N-R5 and one mol. of the other appropriate monoazo dyestuff. They are used for dyeing and printing cellulosic fibres such as cotton, linen or regenerated cellulose. They may be metallized on the fibre and/or in the dyebath, e.g. as in Specification 455,274 or 619,969. The starting materials of the formula R1-N = N-R2-NH -CO-R3-NH2 are made as follows: (1) Amino-sulpho-salicylic acids are diazotized and coupled with H-R2-NH2, the product condensed with m- or p-nitrobenzoyl chloride and the nitro group reduced to amino; (2) sulphonated amines NH2-R2-X are diazotized and coupled with unsulphonated salicylic acids, X then converted into amino, the product condensed with m- or p-nitrobenzoyl chloride and the nitro group reduced to amino; (3) in certain cases the method of (2) may be carried out where X is amino, e.g. with p-phenylene diamine sulphonic acid, only one amino group of which is diazotized. In method (1) H-R2-NH2 may be coupled in the form of its methanesulphonic acid derivative and then hydrolysed. The starting materials of the formula R1 - NH - CO - R3 - N = N - R2 - NH2 are made by diazotizing an aminobenzoylamino-sulpho-salicylic acid (see Group IV (b) and coupling with H-R2-NH2 which may be in the form of its methane-sulphonic acid as above. The starting materials of the formula NH2-R4-N = N-R5 are made by diazotizing an o-chloraniline containing a para-substituent Y, coupling with a salicylic acid and converting Y to amino. In the examples: (1) diazotized 2-chloro-4-nitroaniline is coupled with salicylic acid and the nitro group reduced to amino; also diazotized 5-amino-3-sulphosalicylic acid is coupled with cresidine, the product condensed with m- or p-nitrobenzoyl chloride and the nitro group reduced to amino; the two monoazo dyestuffs are then reacted with phosgene; (2) as in (1) using as second component the monoazo dyestuff from diazotized 5-(m- or p-amino-benzoylamino)-3-sulphosalicylic acid and cresidine; (3) as in (1) using as second component the dyestuff from diazotized 4-nitroaniline-2-sulphonic acid and salicylic acid, reduced, coupled with m- or p-nitrobenzoyl chloride and the nitro group again reduced to amino; an alternative second component is obtained by condensing the monoazo dyestuff p-phenylene diamine monosulphonic acid --> salicylic acid with m- or p-nitrobenzoyl chloride and reducing the nitro group to amino; (4) cotton is dyed with the product of (1). Other suitable components are mentioned. Specifications 555,791 and 583,849 also are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH684527X | 1949-12-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB684527A true GB684527A (en) | 1952-12-17 |
Family
ID=4528752
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29513/50A Expired GB684527A (en) | 1949-12-02 | 1950-12-01 | New disazo-dyestuffs and process for their manufacture |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB684527A (en) |
-
1950
- 1950-12-01 GB GB29513/50A patent/GB684527A/en not_active Expired
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