Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1997-08-05
1999-02-16
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534599, 534634, 534638, 534829, 534873, C09B 4312, C09B 43136, C09B 4316
Patent
active
058722289
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/00296 filed Jan. 25, 1996.
The present invention relates to a process for the preparation of reactive azo dye-stuffs starting from maleylated aminoazo compounds.
The selectivity of the. coupling in the preparation of azo dyestuffs can be controlled, for example, by parameters such as the temperature and the pH (cf. U.S. Pat. No. 5,350,838). In DE-A 32 17 224 (U.S. Pat. No. 4,841,027), a certain orientation during the coupling is achieved by acylating the amino group of naphthalenesulphonic acid coupling components with an anhydride of a dibasic acid, such as maleic anhydride, before the coupling. The aminoazo compounds acylated in this way are then hydrolysed and intermediately isolated before they are reacted further with reactive components to give reactive dyestuffs.
A process has now been found for the preparation of reactive azo dyestuffs which, in the form of their free acid, correspond to the formula (I) ##STR3## wherein
m denotes 0 or 1,
A denotes the radical of a diazo component, in particular from the benzene or naphthalene series, and
X denotes a fibre-reactive heterocyclic radical, (IV) ##STR4## wherein
A and m have the abovementioned meaning, without intermediate isolation, with a reactive component of the formula (VI)
X has the abovementioned meaning and
Hal represents halogen, in particular Cl or F.
In a preferred process procedure, reactive azo dyestuffs of the formula (I) wherein A denotes a benzene derivative of the general formula (II) ##STR5## or a naphthalene derivative of the general formula (III) ##STR6## wherein
R.sub.1 and R.sub.2 independently of one another represent hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or arylazo which is optionally substituted by substituents such as halogen, in particular F, Cl or Br, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or SO.sub.3 H, in particular sulphophenylazo, and
n, o and p independently of one another represent 0 or 1,
In a preferred embodiment of the process according to the invention, compounds of the formula (I) wherein
R.sub.1 and R.sub.2 independently of one another represent hydrogen, chlorine, fluorine, methyl, ethyl, methoxy, ethoxy or 4-sulphophenylazo,
The compound obtained by hydrolysis of the maleylated aminoazo dyestuffs of the formula (IV) probably corresponds to the formula (V) ##STR7## wherein
A and m have the broadest abovementioned meaning.
In a particular embodiment of the process according to the invention, those compounds of the formula (I) wherein
A denotes a benzene derivative of the formula (II) which corresponds to the formula (VII) ##STR8## or denotes a naphthalene derivative of the formula (III) which corresponds to the formula (VIII) ##STR9##
and R.sub.1, R.sub.2, n, o and p have the abovementioned meaning, are prepared.
The process according to the invention wherein compounds of the formula (IV) correspond to the formula (IX) or (X) ##STR10## wherein
A has the broadest abovementioned meaning,
The hydrolysis here is in general carried out in aqueous-alkaline solution, preferably at pH values .gtoreq.10 and temperatures of 60.degree. to 105.degree. C.; bases which are used are alkali metal hydroxides or alkaline earth metal hydroxides, preferably sodium hydroxide, potassium hydroxide or lithium hydroxide.
However, the hydrolysis in aqueous-acid solution, preferably at pH values .ltoreq.4 and temperatures of 60.degree. to 105.degree. C., is of greater importance; acids which are used are, in particular, mineral acids, preferably hydrochloric acid and sulphuric acid. Other process parameters for the hydrolysis are to be found, for example, in DE-A 3 217 224.
Suitable fibre-reactive heterocyclic radicals X, i.e. those which react with the OH or NH groups of the fibre under dyeing conditions to form covalent bonds, are, in particular, those which contain at least one reactive substituent bonded to a 5- or 6-membered aromatic heterocyclic ring, for example to a monoazine, diazine or triazine ring, in particular a pyridine, pyrimidine, pyridazine, py
REFERENCES:
patent: 3225027 (1965-12-01), Baker et al.
patent: 4511507 (1985-04-01), Kayane et al.
patent: 4841027 (1989-06-01), Kayane et al.
patent: 5350838 (1994-09-01), Helle et al.
patent: 5512663 (1996-04-01), Kunde
Le A 22 347, corresponding to DE-A-33 16 984, Process for preparing O-sulphonates of optionally substituted aminoaphthols, pp. 1-8, Nov. 15, 1984.
Derwent Abstract of JP 57-187,361, Nov. 18, 1982.
Derwent Abstract of JP 59-004,653, Jan. 11, 1984.
Bayer AG
Powers Fiona T.
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